


Dare to Imagine a Different Life

by ohreallyjenn



Category: Supernatural, You've Got Mail (1998)
Genre: Alternate Universe - Modern Setting, Alternate Universe - You've Got Mail Fusion, Bisexual Dean Winchester, Books, Coming Out, Dean/Cas Big Bang 2019 (Supernatural), Emotional Infidelity, Enemies to Friends to Lovers, Explicit Sexual Content, Gay Castiel (Supernatural), Love Triangles, M/M, Pen Pals, Slow Burn, Tumblr
Language: English
Status: Completed
Published: 2019-11-11
Updated: 2019-11-11
Packaged: 2021-01-24 14:01:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 16
Words: 33,508
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21339409
Author URL: https://archiveofourown.org/users/ohreallyjenn/pseuds/ohreallyjenn
Summary: Castiel Shurley has been keeping his father's sci fi/fantasy bookstore running in New York City despite the Amazon revolution and with the dedicated help of his quirky staff. He is practically living with this long-term boyfriend, and he maintains a close, yet anonymous friendship with this online pen pal.Since Dean Winchester was born, he has been being groomed to take over the family bookstore business. He has a girlfriend that fits right in with the upper crust; while he indulges in his nerdy side with his best friend and business partner, Charlie, and on his secret account on Tumblr.With the imminent opening of their new location down the street from Castiel's shop, both men are forced to confront their life choices and inner feelings.A re-telling of "You've Got Mail" with a mix of your favorite "Supernatural" characters as well as a few from the original romantic comedy.
Relationships: Castiel & Claire Novak, Castiel/Dean Winchester, Castiel/other male character, Charlie Bradbury & Dean Winchester, Dean Winchester & Sam Winchester, Dean/Other female character, Donna Hanscum/Bela Talbot
Comments: 36
Kudos: 107
Collections: DCBB 2019, DmsilvisFicart





	1. Morning Routine

**Author's Note:**

> This is my very first DCBB and I am so excited for people to read it. I had this idea while re-watching "You've Got Mail" for the hundredth time in my life, and I knew that I would never get it written unless I joined this collection and had a deadline.
> 
> I want to thank my amazing artist, dmsilvisart, for the beautiful and dynamic pieces she created.
> 
> I want to thank my wifey, dozmuffinxc, for being a wonderful and helpful beta. (Even suffering through the smutty parts.)

Castiel’s alarm clock is not given the chance to wake him up today. Instead, like so many other mornings, Castiel’s boyfriend, Frank, has been riled up by something he was reading while the coffee was brewing, and has started the conversation for the day before Castiel is entirely conscious. 

“Can you believe this? It is like humans have ceased evolving, and we are all just letting our technology slowly envelope us like a womb.” Castiel has no idea what that means or how he is supposed to respond, but he is begrudgingly awake now. He lets out a neutral “hmm” to keep Frank’s trajectory moving forward as Castiel props himself up against the heavily pillowed bed.

“It says here that a group of college students at NYU have collected enough signatures to take before the board of trustees to change the school’s policy on allowing professors to prohibit the use of cell phones during their class time. I mean, just look at this, Castiel,” Frank exclaims as he charges into the bedroom and flops down onto the bed next to him, tablet thrust into his lap with the article’s headline on display. “Imagine if these bright young minds had taken as much initiative in trying to change policies to help stop global climate change, or election funding laws, or just anything else. But, no, all future generations including our own are destined to fight for their rights to check out from reality and get forever lost in the shallow waters of social media scrolling.” 

Frank lets out an exaggerated sigh as he takes his tablet back from Castiel, having not even had the time to read the bi-line. 

“Sounds like the subject of your next piece is already in the works,” Castiel dutifully injects with a bemused smile on his face directed at his boyfriend’s back as he finishes gathering his things for work. 

“It is the end of civilization as we know it,” Frank quips as he stoops to grab his messenger bag off the ground by the coffee table. “I’ll let you read the draft tonight. Sushi on 6th tonight?”

“Sushi! Perfect. Have a good day,” Castiel offers as Frank sweeps through the living room and out the apartment door, letting it slam shut behind him.

Castiel leans forward in the bed, cocking his head to listen for Frank’s steps down the stairs. He throws back the covers and plants his feet on the hardwood floor, making his way around the bed over to the window to watch Frank jog down the front stoop and head down the sidewalk. With the coast clear, Castiel can indulge in his favorite pastime/guilty-pleasure: scrolling through his Tumblr feed.

It is not like it would be such a big deal if Frank were to see Castiel on social media. Sure, it would probably be accompanied by some eye-rolling or an exasperated sigh, but Frank isn’t the type of person to be so controlling as to prevent Castiel from doing something he enjoys. But he is definitely the type of guy to make it a lot less enjoyable. Frank may be one of the smartest people that Castiel has ever met, but sometimes all of that intelligence and analysis and discourse can be exhausting. Sometimes, Castiel just wants to take a break and indulge in his fandoms and memes for a bit.

Castiel is also looking forward to checking his messages to see if his favorite on-line friend has sent him something new. An easy, small smile brightens his face when he sees a new message waiting for him from Tumblr user NY1967:

_ Brinkley is my brother’s dog. He got the dog about 6 years ago when he was in third grade. I have to tell you, and many people find this particularly appalling, but I am not a fan of dogs. They can be loud, and smelly, and they jump all over you. Just not my idea of the perfect companion as everyone seems to think of them. However, and I would never tell my brother this in a million years, I make an exception for Brinkley. This dog is better than most people I know. He is soft, and sweet, and when he isn’t providing the perfect listening ear for all your troubles, he mostly just lays around on a pillow the size of an inner tube. Now, I love my little brother a ton. I would die for that mop-headed nerd. But it is getting to the point where I would probably die for that dumb dog, too. Again, not that I would tell my brother this. He doesn’t need any more ammunition against me. You, however, don’t know who I really am or where I live, so I feel safe in letting you in on my shameful secret. But remember, this disgusting love only applies to Brinkley. I would never stoop to loving any other filthy creature._

_ I suppose I’m getting sentimental since my brother is starting high school this year. Fall in the city is always one of the best times of the year. The air gets crisp and the colors change. Students are still excited about classes. New York in the fall is my favorite. If I knew where you worked I would send you a bouquet of freshly sharpened pencils to celebrate this time of year._

Castiel’s eyes crinkle as he reads. Castiel started following NY1967 after a post with a response from him crossed his dash almost three years ago. Castiel honestly can’t remember what the original post was about, but he knows that NY1967’s response made him laugh, so he gave him a follow. Apparently, he is the type of user who likes to follow back, because by the next day, they were mutuals. From there, it quickly escalated into meme sharing and book recommendations. Eventually, they started exchanging inside jokes through direct message, and now Castiel would consider NY1967 one of his closest friends, despite not knowing his real name or occupation. 

Castiel knows he does something with books, just like himself. Maybe an editor or publisher, some sort of family business. He knows he lives somewhere in New York, like Castiel. He knows he is a man about the same age as Castiel. He knows lots of fun little stories and random details about his likes and dislikes. He knows that he is passionate about social justice, but doesn’t get to participate much. He knows his family is kind of big and pretty different. But if Castiel were to pass him in the street, which he very well might have done already many times, he would never know. He has no idea what NY1967 looks like, but that has never been an issue.

Castiel hits the reply button and begins to type.

Dean sits at his breakfast table, sipping his first cup of coffee and perusing the newspaper. He’s got a hectic day ahead of him, but he has at least twenty more minutes before he has to head out. For now, he gets to relax and enjoy the happy buzz he always has after spending some quality time with his little brother, Sam. They spent all of last night hanging out and talking about high school. His relationship with Sammy has always been strong despite their age difference. With Dean being so much older, he has been more of a combination brother and father (with maybe some fun uncle thrown in) to Sammy. Dean hopes that their relationship will stay strong through the rest of the tumultuous teen years. He almost shudders at the thought.

“Oh my God, I’m so late! Did you start the thing?” Patricia comes half-running into the kitchen, blazer already on, heels in her left hand as she grabs her coffee thermos off the counter by the sink.

“Yes, it will be done brewing in…two more minutes,” Dean replies after leaning over to check the machine, no extra urgency added. This is the same frantic rush that greets him most mornings as his girlfriend gets ready for work.

“Ugh! Right, okay. Did you see the opinion piece in the Times by what’s-her-face from Random House? She really put her foot in it this time. So that makes one more person I don’t need to talk to again. Thank god,” she rambles as she shoves manuscripts into her bag. She looks back at the still dripping coffee machine and lets out a frustrated sigh, “I don’t have time for this today!” she exclaims as she scurries out of the kitchen again back to the bedroom.

Dean flips to the next page in his paper and takes another bite of bagel before she reappears in the doorway, coat in hand and shoes on her feet. “Don’t forget that we have the dinner at Philip’s tonight.”

Now Dean meets her eyes with a bit of dread. 

“I have to go to that?”

“Dean Winchester, you promised,” Patricia accuses, not letting him off without a challenge.

“Yeah, but they’re _your_ friends! I mean, what is the cause this time? Can’t I just send a check and avoid the whole schmoozing and soft music and poor beer selection?”

“Oh, you poor baby. Has to get through a nice party with catered food and other adults,” Patricia teases with a pout as she maneuvers in between the newspaper to sit on his lap and stroke the back of his head just how she knows he loves it.

Dean cracks a smile and chuckles into her shoulder. “Okay, fine. I’ll go.”

Patricia leaps to her feet. “Perfect. Be ready by seven.” She quickly pours the contents of the coffee pot into her travel mug, throws a quick peck on Dean’s cheek, and runs out the door.

Dean cautiously puts down his newspaper after he hears the door slam. He walks over to the front door and looks out the peephole to the hallway. He watches as Patricia makes her way into the elevator and the doors close behind her. Dean smiles to himself as he scurries away from the door and goes to grab his laptop off of the coffee table. He flips it open and opens up his Tumblr page.

Dean feels a little guilty that he hides this part of himself from Patricia. He just knows that she wouldn’t understand. She is so invested in her upper-crust and high society circles; the idea of her well-to-do, old-money boyfriend spending time on a social media site for fandoms and queer kids would be appalling. So to save himself the headache of trying to explain why he enjoys it, Dean just keeps it to himself. Besides, it is good to have things that are only for yourself. Couples don’t have to share absolutely everything about themselves to be healthy. Right? Right. 

The last of the lingering guilt is all but forgotten when Dean sees that he has a new message from bookshop-boy:

_ I have to agree that fall in the city is one of the best times of year. I am always so tempted when I get to work to just keep walking for a bit longer, make my way to the park and let a bit of the refuge of nature surround me. When I’m on my favorite path, walking under the changing trees, I hear nothing. Not a sound on the city streets, just the beat of my own heart. Alas, my presence is still always required at work, so my indulgences need to be controlled. However, a bouquet of sharpened pencils sounds like a wonderful solution to the dilemma._

_ Brinkley sounds like a perfect confidante for anyone. And don’t worry, your secret is safe with me. It seems that I have collected many of your secrets over the years. I feel honored to have your trust, even if it is only based on our equal anonymity on here. I often think of our conversations as those between the oldest and dearest of friends. I look forward to your messages so often. I do hope you enjoy these fall days to their fullest, which may even include a certain furry companion._

After Dean finishes reading bookshop-boy’s message, he reluctantly finishes getting ready for work and heads out to the building site. It is true what his friend wrote: Dean often thinks of him as his oldest and dearest friend, second only to his brother and his business partner/best friend, Charlie. Dean never imagined this type of relationship for himself when he was growing up. (Well, relationship may be a bit of a stretch. Dean doesn’t even know the guy’s real name.) His childhood was always so focused on the family business and his inevitable involvement in it. His life always seemed like it was planned out for him before he even took his first breath or had his first thought. His life online is a much needed escape from all of the responsibility of his day-to-day life. And bookshop-boy is one of the best parts of that escape. Dean is often happily surprised when he finds a new message in his inbox. He always half-expects for his online friend to simply disappear into the ether. Dean is never quite sure what keeps bookshop-boy writing to him. Perhaps Dean has something to offer a smart, kind-hearted, creative, literary type like bookshop-boy, but Dean has no idea what that is. 

Dean isn’t going to dwell too long. All he knows is that he is thankful for their messages, and it keeps him smiling all the way to work.


	2. Opening Up Shop

“So, the contractor says that they are on schedule, despite the plumber having to return half of the original pipes because they weren’t right. The painters are going to be here next Wednesday to get all of the primer on after the electrician finishes. And we now owe a fine to the city for some of the disgusting construction workers peeing off the roof!” Charlie ticks off each item on her list as she and Dean make their way through the building site. Dean nods along as his eyes bounce around to the various activities going on.

“That sounds great. Just great,” he responds in monotone, still not focusing on Charlie. “Hey, did you schedule the painters yet?”

“Now see, I knew you weren’t paying attention. I just said they would be here next Wednesday,” Charlie says with a more amused than accusing tone.

“You’re right. I’m sorry.” Dean shakes his head as he turns towards his best friend. 

Charlie and Dean have been friends since college. She has really brought a lot of joy and perspective to his life, something that was seriously lacking when he was solely surrounded by family and business associates. She is spunky and unapologetically real with her life and opinions. It can be tough for her in a stuffy corporate environment, but she is also brilliant at her job and has Dean to back her up.

“What’s on your mind? Something good,” she asks with a hopeful bounce of her eyebrows.

“Ya know, it’s just… ‘I hear nothing. Not a sound on the city streets, just the beat of my own heart.’ Or at least I think that’s how it goes,” Dean remarks wistfully. Charlie turns to face him head on and block his path forward.

“Oh my god! You and Patricia got engaged, didn’t you? Admit it! You are being so weird and romance-y!”

“What? No, no we didn’t. Of course not,” Dean exclaims immediately.

“Okay, okay, fine. No need to throw a hissy fit. I mean, it’s not so far-fetched, is it?”

“Well, no. I mean, I love Patricia. She’s very smart and, uh, energetic. We just haven’t talked about anything like that yet.”

“Okay, cool, cool, cool. Then what’s with the poetic daydreams?” Charlie crosses her arms and arches her brow.

“It’s uh, it’s nothing really. Just something I read that stuck with me this morning. But tell me, have there been any more demonstrators outside since last week?” Dean asks, quickly changing the subject away from his message from bookshop-boy. Charlie may be one of his best friends, and she is one of the few people Dean knows that admits (proudly in fact) that she is a geek and is heavily involved in fandom online. However, Dean still feels there isn’t any need for her to know about his long-term pen pal.

Charlie, to her credit, lets Dean change the subject without anything more than a suspicious glance. “There were a few picketers over the weekend, but nothing serious.”

“It’s almost a bit of a letdown that every time we open a new store, people try to act like they will fight us and don’t want us there.”

“But we always get them in the end,” Charlie adds.

“That we do, my dear. And do you know why?”

“Tell me, sensei.”

Dean chuckles at her. “Because we sell a huge selection of books at discount prices alongside the last legal stimulant: coffee.”

“Well, when you put it like that, we almost seem like we’ve been sent from heaven above,” Charlie quips as they make their way further into the job site.

“I wouldn’t go that far. And we still need to hold them off until we can open. Until then, we will just put up a big sign that reads ‘Coming Soon: a Winchester Books Superstore – The End of Civilization as You Know It.’”

Castiel reaches his store, The Shop at the End of the Universe, to find his sales associate, Claire, waiting for him. 

“Good morning Claire!” he calls to her as he unlocks the security gate and rolls it up out of the way of the shopfront. “Don’t you just love New York in the fall?” has asks blissfully.

Now, Claire tries to be a very tolerant person. She may be more cynical than most, and Castiel, while more cheerful than her, is usually quite surly at such an early hour, but this morning is a bit more than she can bear.

Claire follows Castiel into the shop after he unlocks the door. “What’s up with you? You’re being weird… weirder than normal.”

“What do you mean? I’m just in a good mood, is all.” Castiel answers as he unpacks his bag, placing a large handful of freshly sharpened pencils in a cup and displaying it prominently on the front counter, adding a ribbon around the rim.

“Really? Then what is this about?” Claire asks, picking up the cup with a look of offense on her face.

“Nothing, I just felt like the need for some fresh supplies.”

“Buying office supplies is all well and good, but we hardly ever use pencils, and why do you have them out like a bouquet of flowers? Oh wait, never mind, I get it. You’re in love.”

“No I’m not,” Castiel answers quickly, “Oh wait, Frank, yes, I’m in love with Frank. I’m practically living with him.”

“Then you need to spill, because this whole cheery-kindergarten-teacher impression is getting old fast.”

Castiel takes a deep breath and sighs. It isn’t entirely surprising that Claire is suspicious. He may be able to hide most of this stuff from Frank because he is usually too caught up in his own drama to notice. But Claire, while she tries to put out a tough and apathetic vibe, is really an emotionally intelligent person who cares deeply about a very select few people. Castiel feels honored to be one of those few.

“Okay, but you need to reserve your judgment until you have all the facts. Deal?” Claire moves her fingers across her lips like she is zipping them closed before nodding at Castiel to continue.

“So, I guess it was about three years ago. I started following this guy on Tumblr because he was funny and clever. He followed me back. Then we each started interacting with each other’s posts. Before I knew it, we were kind of friends. Then we started messaging each other funny stuff, and now it is an almost daily occurrence. I get messages from him all the time about his life or thoughts. I send him stories and musings, nothing really serious. In fact, we don’t even send real details about ourselves. I know he lives in the city, but I don’t know his name or what he does exactly. I’ve never seen a picture of him. It is almost anonymous, but it has been going on for so long, I’ve accumulated all of this knowledge about him. It’s strange, because on the one hand, I don’t even know him; but on the other hand, I feel like we are closer than even Frank and me.” 

Claire’s eyes slowly grow larger as Castiel explains. He stands staring back at her for a moment at the end of his speech before she finally responds.

“Dude.”

“I know,” Castiel shakes his head and looks down at the counter. “It’s weird. But it is so nice to talk to him. He’s really a great person.”

“I mean, are you in love with him? Do you have sex?”

“Love? Sex? What? I told you, I don’t even know his name. We haven’t met.”

“So? You can totally have sex and fall in love with someone without meeting them in real life. Haven’t you ever seen that show ‘Catfish’? It happens all the time. Does he know what you look like?”

“No, we are on equal footing on that front. He doesn’t know my real name or what I look like or where I work.”

“This is so crazy. He could be anybody. You could pass him in the street every day and not even know it.” 

The bell over the door rings as Castiel’s other sales associate, Gabriel, walks in, sunglasses on, coffee in hand, and a general look of exhaustion and possible hangover on his face. 

Claire leans over the counter to whisper to Castiel, “It could even be Gabe.”

“No, I don’t think so,” Castiel quickly responds as Gabriel makes his way over to them.

“Hey Gabe, do you have internet friends?” Claire asks, suddenly determined to rule him out as a potential suspect.

“Nah, the internet is just another way for me to feel rejected by women,” he deadpans as he moves to the back of the store to put down his belongings.

After Gabriel is out of earshot again, Castiel leans back over to Claire. 

“See, it couldn’t be him. Besides, I’m thinking of ending the whole thing. It’s getting a bit weird not actually knowing the guy. Plus, I’ve been starting to feel guilty because of Frank. I can’t tell if it is some kind of cheating. But if it makes me feel like this, it can’t be far off.”

“I guess, but you said that it has nothing to do with sex or love.” Castiel hums in response as the bookkeeper, Birdie, walks in the door. Birdie is a short, sturdy Jewish woman in her late sixties. Castiel has known her since he was a kid.

“What are you two whispering about?” she asks as she flips the closed sign over to open.

“Online relationships,” Claire answers easily as Castiel moves to set up the register.

“Oh, I tried those once, but I kept getting sent dirty pictures,” Birdie muses as she makes her way to the back office to start her work. 

Claire scrunches up her nose in disgust as Castiel tries to hide a smile. The bell over the door rings again as their first customers of the day make their way into the shop.


	3. Meeting at Winchester Books Headquarters

Dean made his way into his father’s office. The place was bigger than most apartments in the city. Huge floor to ceiling windows took up two walls of the corner office. John sits behind his desk off to the left while his grandfather, Henry, is seated at his desk tucked into the corner at the far right. Dean settles himself onto one of the couches around a central coffee table before disseminating the latest news to the two leaders of the family business.

“So, sorry to say, but word is that the City Books two blocks up is going under,” Dean states with sarcasm dripping off his words.

“Aww, another independent bites the dust,” John Winchester says with mocking sadness.

“On to the next!” Henry declares.

“We offered to buy out their inventory, mostly your run-of-the-mill fiction,” Dean says.

“How much, son?” John asks skeptically.

“Oh, nothing much, sir. It will do fine at the new store. Until then, we can keep them from caring on a going out of business sale well into our opening weekend,” Dean assures him.

“I suppose. You’ve always been too soft on those people. It has nothing to do with us if their store can’t survive a little competition. That’s what good business is all about.” John says.

“Of course, sir.” Dean says. 

He’s heard this plenty of times before from both his father and grandfather. While Dean may be good at managing projects and people, he has never had quite the ruthless streak that the elder Winchesters have been known for. Dean tries to remind himself often: it’s not personal, it’s business. Someday, it might fully sink in. Dean sees a lot of things in black and white, but when it comes to people’s livelihoods, he often thinks there is a lot of room for gray.

“So what does that leave in the neighborhood?” Henry asks from the other side of the room.

“One mystery book shop – Sleuths, which is holding out, and a sci-fi/fantasy store called The Shop at the End of the Universe.” Dean says.

“Oh, Chuck’s store,” Henry says, mostly to himself.

“What’s that, grandpa?”

“Chuck Shurley’s store. He was a writer, too. Wrote some decent pulp sci-fi about two brothers who hunt monsters. Not a bad series. He was a decent guy, a little squirrely, but a good man. He died a few years back. I think his son owns the store now.”

“Well I can’t imagine that will last much longer,” Dean replies, mostly for his father’s sake.

“I should think not,” John states matter-of-factly, ending the quick detour before Henry can reminisce too much. “There was something else I needed to let you know about, son.”

“Oh yeah, what’s that?”

“Your father is getting married again,” Henry answers for him.

“Ah, how nice. To Bela, I’m assuming?” Dean asks with a bemused note to his voice.

“Yes, Bela. She’s been getting antsy, and it is about that time.” John replies with not even a hint of irony. Dean never understood his father’s approach to romance. Or even his grandfather’s, for that matter. They both treated the women in their lives like a part of their business; something to be cultivated and managed until no longer useful. Bela and his father have been dating for about six months. She is much younger than him (the norm for his father) and she is some sort of small antiquities dealer.

“Well, cheers to the happy couple,” Dean offers before he heads back out of the office.

Message from user – NY1967, Sept. 15th:

_ My father is getting remarried again. It is to the point that I need to count out the names as I think through them to remember how many it has been. I’m certain that he loved my mother, his first wife. And I’m pretty sure he loved, or at least had strong feelings for, my brother’s mom. The later ones, who’s to say? He may feel something that he thinks is love for them, but for the most part the relationships are about status and appearance. The one he is currently engaged to is only a few years older than me. She has a fancy accent and a fancier job. She knows exactly how to dress to all of the fancy gatherings. It is an easy choice for him. _

_ My grandfather is another story. He was married to my grandmother for nearly forty years before she passed. It wasn’t until after that he started going for younger women. His latest wife is younger than me by 3 months._

Message from user – bookshop-boy, Sept. 18th:

_ When I was a kid, I read a book about a butterfly on the subway and today, I saw one! She got on at 28_ _ th _ _ and off at 59_ _ th _ _. Which probably means she was going to visit Bloomingdales where she will buy a hat that will ultimately be a mistake. As hats so often are._

Message from user – NY1967, Sept. 24th:

_ I got approached by one of those salesmen on the street today that target tourists. He came right up to me and said I looked like I was not from the city because I was looking around and I seemed happy. Now, obviously he was dead wrong and I laughed and kept moving, but I wonder if it is true. I know the tourists can sometimes stick out, but I never really looked at the people who seem to blend right in. Are New Yorkers really so numb to it all that they don’t even look around at their own city when they walk? I’m sure I’ve done this before when I am in a hurry, but I find it hard to completely shut out what is around me, especially when so much of it is so interesting. I’ve lived here my whole life and I don’t think I will ever run out of reasons to look around._

Message from user – bookshop-boy, Oct. 1st:

_ Most people who live in the city avoid places like Time Square and the like as much as humanly possible. They are loud and crowded and there are so many better places to be. But I have to say, when I need inspiration for a character, these are the first places I go. They are built for premium people watching. There are families, couples, foreigners, businesspeople, workers of all classes, and performers. Any type of person you want to study, you can find there. If you are stuck for whom to put in your next scene, it is guaranteed you will find someone new on the sidewalk there debating which musical is worth waiting in line for. If you don’t know how to create the family dynamic you are searching for, there are at least ten different families having ten different calamities on the street as I type this. I guess you could say that one man’s anxiety-inducing crowd is another man’s cure for writer’s block._

Message from user – NY1967, Oct. 8th:

_ There is this bakery near my apartment that gets its flour delivered in the evenings via a truck and huge tube down to their basement. Every time, it leaves this plume of flour that floats like a fog through the air. It never seems to settle on anything, but is always gone by the morning, now turned into my favorite bagels._

Message from user – bookshop-boy, Oct. 13th:

_ You ever find yourself re-reading the same series for comfort? I know for lots of people that series is Harry Potter, but for me, I can always pick up anything from the Supernatural series. It is a bit melodramatic (one of its best features, I think) and just scary enough to leave me in suspense. Granted, the frustration that I so often feel about the brothers’ co-dependent nature can sometimes sour the experience. If you haven’t read the series yet, I think you would love it._

Message from user – NY1967, Oct. 23rd:

_ Places like Starbucks are built for those kind of people that are completely incapable of making decisions in their real life. Think about it: you got thousands of people filing in that on a normal day go back and forth with their partner on where to eat for so long that they both could potentially starve to death, but in Starbucks, they walk in and make at least five rapid decisions in a row. Caf, half-caf, de-caf, whip, no-whip, dark roast, light roast, blond, tall, grande, venti, extra pump. Someone who has never committed to anything in their life can for the small price of just about $5 feel like the master of his domain. Tall, de-caf, light-whip cappuccino!_


	4. But They Discount

Gabriel is making his way to work on a brisk Tuesday morning when he spots it. He knew there was some sort of big construction going up about two blocks from the shop, but he never bothered to check what was going on. Now it was all too obvious with the huge sign that had gone up overnight: “Winchester Books Superstore – Coming Soon!”

“It’s not going to be a problem. They are big and gaudy and generic and soulless. We have been around long enough that people know us well,” Castiel reassures the whole group after their worried faces turned to him at Gabriel’s news. Gabriel had come into the shop like he’d seen the beginning of the apocalypse. Meanwhile, Castiel had already noticed the superstore going up and had decided to not let it get him down.

“But they discount,” Gabriel says, as if it is a special weapon or supernatural power. As if Castiel doesn’t already know that. Plenty of business had already been syphoned off from online sales. What is one brick and mortar place going to do that Amazon hasn’t done already?

“With the amount of hipsters in this area, no way they are going to give their business to some huge chain. They value the quirky and diverse, not the conglomerated blandness that is a Winchester Books. The neighborhood will most likely protest them or roll their eyes and ignore them. In the meantime, I’m going to remain positive and schedule some fun events.”

“As well you should. No need to let them get to us,” Birdie adds with a nod. 

Gabriel doesn’t seem entirely satisfied with the response, but he vacates the front counter nonetheless. Claire also still seems apprehensive as she follows Gabriel away from the group. Castiel waits until they are out of earshot when he leans over to Birdie. 

“We are going to be fine. Right?” he asks with just a hint of trepidation leaking through.

“We’ve managed to keep this store open through all manner of evolutions and upheavals. But, of course, not without a fight.”

“Of course you have to fight, Castiel. There is nothing that stands in the way of these overinflated capitalist cogs except ordinary citizens standing up for themselves.” 

Frank is immediately energized by Castiel’s account of the discussion earlier that day. But, then again, Frank lives for the fight for justice for the little guy. It is what first drew Castiel to him at the start of their relationship. Castiel has always admired his boyfriend’s seemingly indefatigable pursuit for equality. Today, though, when that pursuit involves centering Castiel’s store in the larger fight against corporate capitalism, he wishes that Frank used a bit more discretion when choosing his battles.

“I understand what you are saying Frank, but I’m not sure I’m up to this kind of fight. The store has been doing just okay for a while now. We have survived the online revolution, but just barely. I’m surprised that a Winchester Books is even opening at a time like this. They probably will only survive based on the Starbucks inside and impulse purchases. This may be a sign that the shop is becoming obsolete.” 

Castiel is already exhausted from the stress of thinking about the situation all day. He was hoping to have a relaxing evening at home, but Frank had already come back from work with more energy than usual because he had obtained a new electric typewriter to add to his growing collection. The guy had a serious problem, but Castiel was not one to judge another person’s harmless obsession.

“Castiel, I think you are giving up too quickly.”

“But how long do you expect me – “

“Castiel!” Frank interjects, a look of sudden inspiration across his face as he snaps his fingers. “Castiel, you are a lone reed.”

“I’m… a lone reed?” Castiel asks with thinly veiled skepticism.

“Yes, you are a lone reed,” Frank confirms as he sits down at his beloved typewriter and scrolls a fresh piece of paper through it and begins to type. “You are a lone reed… standing tall… waving boldly… in the corrupt sands of commerce,” he finishes with a flourish as he whips the page out of the typewriter and hands it to Castiel.

Castiel takes the page from Frank and moves back to the bedroom, muttering to himself, “I am a lone reed… a lone reed.”

Message from user – bookshop-boy, Oct. 28th:

_ I like to think of myself as a good person, but I’ve never considered myself one of particular power or significance. I live a small life, but it is a decent one. I have good friends and I enjoy my work. I think that I make a small difference to few people. _

_ It is probably easy to wish for a grander life in this day and age with social media telling us that everyone around us is having a better time than you. I never felt that fear of missing out when looking at people’s pictures of their travels or delectable meals. But when I see people causing good change in the world, I wonder if that could be me. Sometimes I wonder if my life is small because that is what I want, or is it small because I haven’t been brave?_


	5. The Shop at the End of the Universe

“Dean!” comes the combined scream from two warmly dressed kids as they make their way through the almost complete construction site of Winchester Books. Dean is already smiling when he turns around to scoop Anna up into a big hug and give her a kiss on the cheek. He puts her back on the ground before he forces a hug on his begrudging brother, Sam.

“Don’t I get a kiss? I’m going to be your wicked step-mother soon,” Bela says with a smirk and a swish of her hips as she approaches with another woman that Dean doesn’t recognize by her side.

Dean leans forward to give her a quick peck on the cheek to get it over with. Despite Bela being beautiful and brilliant, she has always made Dean a bit uneasy. Maybe it is the fact that they are practically the same age while she is now marrying his father. Maybe it is her overly-expensive taste and snooty demeanor. Luckily, he doesn’t usually have to spend much time with her.

“Bela wanted to take us shopping for new furniture for the house, but we said that we had plans with you today,” Sam says quickly. Dean has no recollection of such plans, not that he would say no to hanging out with the kiddos. Clearly, Sam was desperate to get away from Bela for the day, and Dean is happy to be used in the escape plan.

“Oh yeah, of course. Yeah, I was going to take the kids out today because I’m mostly wrapped up here. Does that work for you?”

“That works fine. I guess your father didn’t know about the plans because he told me that I would be entertaining them for the day. This works better though, lots of errands to run. But I can leave Nanny Donna with you to help.” Bela indicates the quiet, smiling, plump woman by her side.

“Oh, hi. Nice to meet you,” Dean replies, extending his hand out to her. “But that won’t be necessary. I can handle the kiddos for the day.”

“Nanny Donna is getting a divorce,” Anna adds apropos of nothing. While Anna is a very sweet child, she is still in that stage of over-sharing in polite company. Nine-year-olds can be incredibly honest even when you don’t need them to be.

“Oh, I’m so sorry to hear that,” Dean says with what he hopes is the right tone to reassure someone he just met without coming across as creepy or cold.

“Oh, don’t be. I learned my lesson. Never marry a man who lies,” she exclaims with a giggle.

“Well, that’s just great advice for everyone, isn’t it, guys?” Dean laughs as he looks down at Sam and Anna.

“Well, I’ll leave you all to your gallivanting. There are plenty of things I need to get done,” Bela says as she readjusts her gloves and bag before heading off with Nanny Donna back out of the building.

“So… Tell me. What are these amazing plans that we have today?” Dean asks Sam, not able to hide the smirk on his face.

“Listen, I’m sorry, Dean. But I didn’t want to spend my whole Saturday looking at fabric swatches. You don’t have to do anything with us. Anna and I can just go see a movie or hang out here, out of the way.”

“Well, lucky for you, I wasn’t lying when I said things are wrapped up here. So, the day is ours. What do you say we grab some food that is terrible for us and find something weird to do?” 

Anna’s smile lights up the whole room.

After a hardy meal at a diner nearby, Anna spots a bunch of people dressed in long black robes and colorful scarves. Dean decides they should follow them and they all end up in one of the last few independent bookstores left in the neighborhood – The Shop at the End of the Universe. The chalkboard sign outside tells them that it is the monthly Harry Potter Saturday which they soon learn features cosplay, warm butterbeer, and an animated reading from one of the books in the series.

Now, Dean enjoys Harry Potter as much as the next book nerd. It is an awesome series that he got to grow up reading. But having them read aloud by a gravel-voiced, enthusiastic, sweater-vest adorned man is a far more pleasurable experience than Dean could have imagined. Not only is this man’s reading voice wonderful to listen to, but he does great voices for each character. His Hagrid is particularly spot on, as is his Snape. Dean was just as much engrossed in the reading as Sam and Anna, maybe more so. When it ended and the crowd dispersed, Dean couldn’t explain why, but he felt the need to stick around and get to know the reader. Luckily, Sam and Anna were always happy to explore a book store. You would think practically growing up in one that they would be tired of it, but books are in their blood.

Anna ends up beating Dean to the punch, though, when she approaches the man and asks him about the Terry Pratchett display at the front of the store. They disappear together to discuss Discworld and Dean decides to wait back with Sam instead.

He finds Sam talking with the cute young associate by the butterbeer whose name tag reads “Claire”. Dean has every intention of going over to embarrass him, but resists when he overhears their conversation.

“… it is a reference to the second book after _Hitchhiker’s_ – The Restaurant at the End of the Universe,” Claire answers as she takes a sip.

“Hmm, I’ve never heard of it,” Sam answers simply. Claire looks down right offended before she schools her face.

“Well, let me show you where you can find our Douglas Adams books. He is one of my favorites; very sarcastic and clever. I’ve always admired his take on what would be the worst way to torture any living being in the universe. It’s described in the first book…” Claire leads Sam away to another aisle and Dean is left to wander on his own.

He supposes that he should be doing reconnaissance while he is in the shop. This is one of the last hold-outs for the neighborhood. He’s trying to recall what his grandfather was saying about the store. It is quite a charming and engaging place. Even without the extra flare of the Harry Potter event, the store is well organized and utilizes its space efficiently. It has a great selection for being designated to one genre, and the staff seems well trained and generally happy to be there. Dean figures he should probably check up on Anna.

“I guess I’ll just get the first three for now, but I really want all of them,” Anna says, gathering books up into her hands.

“Oh, well there are 40 some books in the whole series. Maybe you should hold off until you see if you like them,” the man replies with a bright smile.

“My dad gets me as many books as I want,” Anna says as Dean comes up beside her, taking the books from her hands. The man looks over at him at him with bright blue eyes.

“That’s so thoughtful of your dad,” he says while looking straight into Dean’s eyes.

“Oh, that’s not my dad, that’s my nephew,” Anna states matter-of-factly.

The man tilts his head to the side and narrows his eyes at Dean before looking back over at Anna. “Really? Your nephew? Don’t you mean your uncle?” 

“No, actually, she’s right. Anna is my aunt,” Dean smirks at the adorable look of bemusement on the man’s face.

“Well, now you have me curious. I must know all the family secrets,” the man jokes as he turns his eyes back to Dean.

“Well, Anna here is my grandfather’s daughter. And Sammy, over there,” Dean turns to indicate the young man still chatting with Claire, “is my – “

“No, wait. Don’t tell me,” Cas interrupts, mirth on his face as he turns back to Anna. “Is he your uncle?”

“No,” Anna answers with a big smile and a shake of her head.

“Okay, is he your grandfather?”

“Noo,” she giggles.

“Your second cousin twice removed?”

“Nope,” Dean answers while Anna continues to laugh.

“Okay, one last guess and I give up. Is he a tree spirit that you stole from a sacred wood that has taken residence in a teenage boy in order to complete a secret mission?” 

Dean throws his head back and lets out a loud laugh. It is probably inappropriate for a book shop, but he just can’t hold back. He can see that it catches Sam’s attention as he makes his way over to the group.

“No, no. Ha! That kid had homework to do and couldn’t come along,” Dean says between laughs. He suddenly finds himself a lot closer to the man than he was before.

“Ahh, I see,” the man nods feigning serious concern. “It is always important to maintain that grade point average when you are waiting for the next moon cycle to start.” 

Dean manages to hold back his laughter enough to not draw too much attention to them.

“So true. But sadly, that was your last guess. This young man is my brother. Half-brother, technically. We are a big, blended family,” Dean explains, earning another smile when he claps his hand on Sam’s shoulder.

“Well, I’m glad you joined us for our reading today. I’m Castiel Shurley,” he extends his hand to Dean, “the owner. It’s nice to meet you…”

“I’m Dean,” he replies, keeping Castiel’s hand in his. “Uh, just call me Dean.” Sam gives him a side glare for acting strange, but doesn’t say anything. “This is a nice place. Have you owned it for long?”

“About seven years now, ever since my father passed away. It was his shop originally and he left it to me, and I hope I can leave it to my kid,” Dean finally remembers to let go of Castiel’s hand as he motions for them to move over to the main counter. Sam has a book in his hand to add to the pile Dean took from Anna.

“I’m sorry about your dad. But that’s nice to keep it in the family. Does your wife like the idea?” Dean asks.

“My wife?” Castiel looks at him confused for a second. “Oh, no, I don’t have any kids yet. My boyfriend and I haven’t really discussed it. It’s just a hope I have for the future. I’d like to keep the spirit of the shop alive. My dad really liked it, but his passion was always split between the shop and his own writing. Here…” Castiel reaches to the shelf behind the counter to hand Dean a fresh paperback book.

“Oh, the Supernatural series. I heard about this recently, actually. They said it was good,” Dean says and he examines it.

“That’s my dad’s series. He wrote it under his pen name, Carver Edlund. He was pretty prolific and got a decent cult following. But some of the books are out of print now.”

“Well, Cas, why don’t you go ahead and add this to our little horde and you can ring us up,” Dean says placing the Supernatural book on top of the pile on the counter. Castiel starts ringing them up when one of the other associates with “Gabriel” on his name tag slides in next to Castiel by the register.

“You’re going to come back, right? It seems like you like what we have going on here,” he says, looking from Dean to Anna and Sam as well.

“Oh yeah, we’ve had a great time here,” Dean quickly answers.

“See. This is why we are going to survive the Superstore Apocalypse. Because we make people happy,” he says to Castiel.

“What do you mean?” Sam asks.

“Oh, they’re putting in a Winchester Books up the street,” Castiel answers as he hands Dean his bag of purchases.

“Oh, Winchester Books! My dad – “ Anna starts before Dean rushes to scoop his hand over her mouth.

“ – Likes to buy discount. But you don’t need to announce that. Remember how we talked about not over sharing,” Dean admonishes as he give her a “be cool” look.

“Well, they may have better discounts than we do, but we’ve been here over forty years, so I’m not going to let some soulless corporate chain intimidate me,” Castiel answers with determination.

“Well, uh, good luck… and thanks for all the books, Cas… have a great night, or day, or whatever,” Dean mumbles as he tries to herd Sam and Anna out the door.

Back outside on the sidewalk Dean takes a deep breath and shakes his head a bit to reset. He’s not sure why he had to make things so awkward at the end. Why did he go out of his way to lie to Cas about who he was? There is no law that says he can’t go into a competitor’s store to shop. It’s not like he was looking for secret intel or anything. But there was just something about that man that made him wish that he wasn’t Dean Winchester of Winchester Books for a moment. He just wanted to be Dean, a guy who likes books and nerdy things and likes to chat with nice shop owners. Maybe Dean just needs to find more friends. Needs to hang out with people that aren’t his family or his staff. Or maybe he needs to finally give some thought to why he couldn’t stop staring at Castiel’s eyes or want to let go of his hand.

No. Nope. Definitely not thinking about that right now. Moving on.


	6. Something to do With Books

“Would you look at this? No protests or demonstrations,” John Winchester says delightedly as the group makes their way through the main lobby of the newly opened Winchester Books Superstore.

“The neighborhood loves us,” Charlie adds, checking off items on a clipboard as they go.

“It’s a hit!” Henry exclaims.

“They are wondering where we have been all their lives,” John says, turning to Dean. “So tell me, son. How do the numbers look so far?”

“About as expected considering it is still early for too much holiday shopping. We still have two other book stores in the area that are open. It looks like the mystery shop is taking a down turn, but the other one, The Shop at the End of the Universe, is still hanging on. We may want to consider changing out our featured section for something more tailored to the neighborhood. Right now, we are featuring writers from New York, which is all well and good, but I don’t think it is particularly speaking to our clientele.”

“I was thinking the same thing, actually,” Charlie interjects. “I thought we could feature some LGBTQ authors and stories. The neighborhood is very queer friendly and I think they would find it a good gesture by the store.”

“I don’t think that’s such a good idea. Maybe during June or something, but for now, we don’t want to make such a bold statement so early and so close to Christmas. For now, let’s stick to what we know works,” John says, patting Charlie on the shoulder briefly before turning down one of the aisles with Henry following.

Dean doesn’t even try to hide the cringe on his face. “Sorry about that, Charlie. You know how he is. Never one to stick his neck out if it doesn’t guarantee big profits.”

“Yeah, sure, whatever. I knew it was a long shot. I just figured I would try while he was in such a good mood.” Charlie shakes her head and buries it back in her clipboard. Dean pulls her into a side hug.

“Chin up, kiddo. The store is doing great. We will work on the old fogies again soon.”

“Are you sure we shouldn’t try to get a rally going? I’ve got plenty of friends who would cause a ruckus for a lot less. We can get signs and stuff together. Fight the corporate power,” Claire offers as she holds up the tangled string of twinkle lights for Castiel.

“Thanks sweetie, but that’s not necessary. They are a novelty. Their popularity will fade out by the end of the month and then we will move on. We are still doing just as well, aren’t we Birdie?”

“Well, dear, we did $1200 less than this same month last year,” she calls from the back office computer.

“You’re kidding me,” Castiel remarks as he drags the lights along with Claire to get a look for himself. “Well, that could just be a fluke, couldn’t it?”

“It could be… or not,” Birdie warns.

“See, Castiel! We need to do something because I really need this job. If I can’t pay my rent, I’m going to have to move… to Brooklyn!” Claire whines.

“Ahh, the beauty of rent control. Two bedroom and a doorman for $550 a month,” Gabriel sing-songs from the front counter.

“Don’t do that. That’s so rude. It’s like people who brag because they’re tall,” Claire calls back to him.

“If that’s some sort of cheap shot at my height – “ Gabriel shoots back.

“Hey, hey. Calm down. No need to get ahead of ourselves. We are still doing just fine. In the meantime, I’m going to put up more twinkle lights,” Castiel placates.

“Ya know, this place is a tomb. I’m going over to the candy shop where it’s fun!” Gabriel announces as he leaves in a huff out the front door.

“Gabriel?” Castiel calls. “Gabriel?” Castiel walks to the front of the store this time leaving Claire behind to deal with the string of lights. He makes it to the front window when he spots a local author that is a friend of the shop. “Oh, Miranda! Hey, come on in!” he calls to her as he opens the door.

“I wasn’t sure if you were open. Are you doing okay? Are you surviving?” she says in a hurried panic as she makes her way into the shop. Castiel tilts his head at her frenzied demeanor. She has always been one for the dramatic.

“Of course, we are fine,” Castiel says with an easy smile. “Right Birdie?” he calls to the back.

“Not a bit of difference!” she hollers from the office.

“Oh thank goodness. I was so worried that that awful store would have ruined you. Well, just know that I am up to help with anything: protests, picket lines, letters to the editor. Or maybe we can get that nut from the Observer to write something,” she adds with a flourish as she makes her way back towards the exit.

“The uh – what ‘nut from the observer,’” Castiel asks, throwing up air quotes around the words.

“Frank something-or-other. The one that is so in love with his typewriter. This is just the sort of thing to rile him up!” 

Claire covers her smirk as Miranda makes her way out the door.

“She called me a nut?” Frank asks, offense clear in his voice as he holds the door open for Castiel as they make their way into an apartment building. Castiel tries not to roll his eyes.

“That’s not the point. I wanted to know if she was right. Do you think an article by you would have some influence over the situation?”

“I mean, sure. My readers are always up for fighting for the underdog. This would be right up their ally.”

“And it wouldn’t be a complete conflict of interest?”

“No.”

“So, you’ll do it?”

“Yes. Yeah, sure.” 

Castiel sighs with relief. “Good. Thank you,” he says and pecks Frank on the cheek. At least Castiel can go to bed without feeling completely powerless.

“So remind me, what is this party about?” Castiel asks as he adjusts his tie yet again on the way to the apartment door.

“I told you last night, it’s a book launch after party… or he sold a manuscript… or wait, maybe he bought someone else’s manuscript…” Frank rambles.

“So… something generally book related, you’re saying.”

“… Yeah!” Frank responds with ironic mirth. Castiel smirks at him before knocking on the door. They are led inside and greeted by some of Frank’s friends from the paper.

One room away in the same apartment, Dean is struggling to concentrate on a conversation between his girlfriend, Patricia, and some pretentious art critic. Luckily, Patricia wafts her empty wine glass under his nose, giving him an excuse to make his way over to the bar to get a refill. He requests a white wine for her and a beer for himself, and as the bartender turns around, another man steps up beside him. Dean turns to acknowledge him and the greeting dies on his tongue. Standing next to him is none other than the completely charming and also recently mislead shop owner, Castiel Shurley.

Castiel, to his own credit, lights up when he sees Dean standing next to him. “Hey! I don’t know if you remember me – “

“Of course I do, uh, Cas,” Dean answers quickly.

“It’s nice to see you. How is your aunt doing?”

“Ha ha, yeah, she’s good,” Dean can’t hold back the smile at knowing Castiel remembered his family. The bartender turns back with his drinks and hands them off.

“Wonderful, so good to hear.”

“Yes, well, you’ll have to excuse me I need to get back to my date with her drink. Good to see you Cas.”

“You too, Dean,” Castiel replies with a small wave. 

After acquiring his own drink, Castiel makes his way back towards Frank and in the process, he runs into the host of the party. 

“Oh, thank you for inviting us.”

“Of course, any time. I have to say, though, I was surprised to see you chatting so nicely with Dean Winchester.” 

Castiel’s face contorts in confusion and he whips his head back to look for Dean in the crowd again.

“Winchester? As in – “ Castiel responds, disbelief on his face.

“As in – he’s going to take over everything,” he muses as he wanders away to another group of people.

Castiel can’t wrap his head around it. His meeting with Dean a few weeks ago has been on his mind for a while. Dean was certainly handsome and charming. Castiel could never resist a guy who was good with kids. He can’t deny that he hoped he would see Dean in his shop again, but now he feels like there are rocks sitting in his stomach. Castiel doesn’t want to believe that he could be so easily charmed by some pretty rich boy, so he doesn’t stop himself from walking over to the buffet table to confront him.

“Winchester? Your name is Dean Winchester?” Castiel says while grabbing a plate out of nervous distraction.

Dean fights the cringe on his face. He doesn’t want to cause a scene, especially with Patricia and all her friends around. He feels the blush rise on his cheeks. He knew that the friendliness between Castiel and him was going to be short-lived. It was only a matter of time before a nice guy like Cas realized who Dean really was. He takes a deep breath and settles in to meet Castiel for real this time.

“Yes. Dean Winchester.”

“As in Winchester Books? As in the very same store that you and I discussed in my shop just a few weeks ago? As in the… the… the corporate bane of my existence?” Castiel says, getting more flustered by the second. Dean thinks he looks rather cute when he gets mad, but now is not the time to let that thought in. “Why did you lie to me? Why not just tell me who you are?”

“I never lied. I just… didn’t tell you the whole truth,” Dean offers defensively.

“A lie by omission is still a lie. What were you doing there any way? Trying to spy on my shop or something?” Castiel starts to fill his plate with whatever is closest, not really watching what he is doing as he stares down Dean in his, admittedly gorgeous, green eyes.

“I have no need to spy on your shop. Don’t fool yourself into thinking I’m some evil mastermind,” Dean tries to explain as he grabs a plate for himself and starts to peruse the spread. “I was just having a nice day out with some of my family and we followed some oddly dressed people into your store. And it is a charming little shop. You sell what… $350,000 worth of books per year?” 

Castiel stops dead and turns fully towards Dean.

“How do you know that?”

“I’m in the book business,” Dean answers with a bit of smugness.

“No, _I’m_ in the book business. You, in your, your overpriced suit and, and, and… overpriced coffee, selling cheap books - ” Castiel struggles through his anger before Dean cuts him off.

“Now don’t go blaming me for all of your grievances.” Dean has heard this kind of thing his whole life. He knows most of the world sees him as some spoiled rich kid running the family business. And although Dean doesn’t always agree with what his father chooses to do, he knows that the man has worked hard and been careful to be successful. “I’m just a guy who runs a business. Yes, I sell cheap books. How is our business any less valid than shopping at a Price Club instead of some organic Whole Foods? We have the same product, but ours is easily accessible to the masses. And as my father and his father often say, it is what keeps our society going. The market evolves and unless you evolve with it, you shouldn’t be surprised to get left behind or run over.”

Castiel feels as if he actually has been run over. He is frozen in anger, not entirely sure how he ended up face to face with Dean with a knife in his hand. Castiel is not a violent man, far from it, but he is not entirely sure what would have happened if Frank didn’t show up at his shoulder at that moment.

“Hey, how you doin’? I’m Frank Navasky,” he says extending his hand with a warm smile, seemingly oblivious to Castiel’s imminent aneurysm.

Dean takes his hand as he keeps a careful eye on Castiel. “Hi, Dean Winchester.”

“Winchester? As in Winchester Books?” 

Finally Castiel can collect himself enough to let out his breath. Now that Frank knows who they are dealing with, there is no need to be left to fight by himself. 

“Ahh, the inventor of the superstore. The enemy of the mid-list novel, the destroyer of City Books. Tell me, really, how do you sleep at night?”

“Oh, you’ve got to try the new over-the-counter one, EZ-drowse,” comes Patricia’s answer as she appears at Dean’s side seemingly out of thin air. “Don’t take the whole thing, just half. It has done wonders for my insomnia.” 

The intrusion has thrown Frank off his rhythm, and not one to ever be called rude, he introduces himself.

“Hi, I’m Frank – “

“Yes, Frank Navasky. I know your work.” 

Frank moves in closer, “Really?”

“Yes, and can I just say, your article last month was just brilliant.” 

Castiel would usually have walked away from a conversation like this, but to see Dean’s date gush over his boyfriend is extremely satisfying.

“Oh, my, really? Well, thank you. Ya know, when you write these things, you never know how they are received. You usually never hear anything unless it’s bad news.”

“Well, I loved it. I’m Patricia Eden – Eden Books,” she says, turning to Dean, “Honey, this man is the greatest living expert on Julius and Ethel Rosenberg.”

“Oh, huh, well, that’s nice of you to say,” Frank blushes. 

Dean attempts to introduce Castiel but is interrupted by Patricia again. 

“You know what always fascinated me about Julius and Ethel Rosenberg? It’s how old they looked when they were really just our age! Isn’t that strange?” 

Castiel is very proud of himself for not laughing out loud, but the embarrassment on Dean’s face is enough to keep his head held high the rest of the evening. Undeterred, Patricia continues.

“Have you ever thought about writing a book?”

“Ya know, it has crossed my mind. Maybe something relevant for today like the evolution of the barter system though medieval Europe…” Frank continues, but Castiel is already tugging his arm to try to escape this monstrosity of a conversation. Dean decides it is time to disengage as well and pulls Patricia back to her friends on the other side of the room.

“Well, call me if you want to talk about your ideas,” Patricia calls back as she is maneuvered away.

Later that evening, Castiel receives some comfort from Frank as he laments the terrible encounter. Frank may have lost his way at the party with the distraction of a fan, but he at least knows to make Castiel a mug of tea and listen quietly once they are back at his place. While Castiel has his concerns about the endeavor, he is more certain than ever that he is justified in his plans to take on Winchester Books.


	7. Letters and Zabar's

Message from user – NY1967, Nov. 12th:

_You ever feel like you have become the worst version of yourself? I try to be a decent person. I’m good to my family and I work hard. But sometimes I get so lost when defending myself. Someone comes along, perfectly decent human being, but they question my purpose and life and I have to dig in. Putting an asshole in their place is immensely satisfying;putting a good person with a different opinion in their place may feel good at the time, but the guilt comes raging in soon after. My father was definitely the one to teach me these easy intimidation tactics. He taught me to stand up for myself and fight back. It is very useful in business, but when applied to real life they just make me turn into someone nasty. I have a lot of respect for my father, but I’ve always secretly hoped that I wouldn’t become him. Right now, I feel like it has already happened._

Message from user – bookshop-boy, Nov. 13th:

_I know exactly what you mean, and I am so jealous! You seem to at least have the ability to express yourself when confronted. Whenever I get in one of these situations where I want to defend myself, I always get so flustered that I can barely reply back. My mind just goes blank. Often, days later, I will finally come up with a biting come back. I’ve always wished that I had the ability to be able to say exactly what I want to say, exactly when I want to say it. _

_ For what it’s worth, I feel I have gotten to know you the last couple of years, and, to me, you seem like a very good person. You are smart, kind, and thoughtful. While your day to day life may necessitate that you act more like a tyrant when provoked, I hope that you remember that you always have a choice. Perhaps it won’t yield as lucrative results (which has been the data presented in my life, at least), but choosing kindness over getting in the last derisive word will preserve your lovely soul. Take care of yourself._

Message from user – NY1967, Nov. 15th:

_Thank you for your sweet note. I’m not sure what about me on this site has given you the impression that I am all the things you wrote, but I am thankful that you see them even when I can’t. Sometimes, I feel like my real life is on a different planet than who I am here. In my real life I am always being pushed and pulled in directions. I know that technically I can make choices on how to live my life, but with my family obligations, it doesn’t always feel true. I’m sure you have no idea what I’m talking about. I have always admired how open you are about who you are. From your stories and posts, your life seems to allow you to live freely as yourself. Lately, I have been feeling guilty for the great difference from what I present to the people who know me, and what I feel in my heart._

Message from user – bookshop-boy, Nov. 16th:

_I’m sorry you feel like you need to hide yourself from those closest to you. It reminds me of myself a bit before I came out to my dad. I’m lucky that my dad was always a liberal and accepting guy, but even with that reassurance, I was still apprehensive about telling him that I’m gay. It went well, but it wasn’t until after I told him that I realized how much I had been hiding and holding back. I hope that comparison doesn’t make you uncomfortable. I would never assume your sexuality or that it has anything to do with what you are feeling in your life. I do assume that you are accepting of me, though. Seeing as I have never really hidden that from you and you have never said anything otherwise._

Message from user – NY1967, Nov. 17th

_Thank you for sharing that, and no, I’m not uncomfortable with you being gay. It seems a little crazy that you made that connection though. Maybe you know me better than I thought. This has nothing really to do with what I was talking about in my last message, but I guess it does a little. I’ve never told anyone in my real life, but I realized some time ago that I’m not really straight. Now, on a site like Tumblr, that’s not really a surprise. Haha. But to the people in my real life, I think it really would be. I’ve never found it necessary to tell anyone. I’m attracted to women enough that it never caused a problem with my love life. I guess that would change if I met a guy I liked, but I’ll cross that bridge if I come to it._

Message from user – bookshop-boy, Nov. 18th:

_Thank you for trusting me. I feel really honored to be the first person you have told. I don’t want to make a big deal out of it if you don’t, but just know that I’m proud of you and I’m here for you. Maybe, some day, I’ll be able to give you a hug and say welcome “out” in person._ _But I know you’re not one for too much mushy stuff, so I’ll leave it at that for now._

Now that Castiel knows who Dean Winchester is, it is like he can’t escape him. Everywhere Castiel goes, there is Dean Winchester. Picking up flowers at the market – Dean Winchester. Getting some take-out from the deli – Dean Winchester. Petting a cute dog on the sidewalk – Dean _frickin’_ Winchester.

Castiel is picking up the last of the ingredients for his “Friendsgiving,” as they call it, a little tradition they created a few years ago and one that he always looks forward to. He is in Zabar’s Grocery getting the hummus that Birdie loves when he spots him yet again. Dean Winchester is like glitter, only worse, because at least glitter is tiny. Dean is some gorgeous, tall drink of water that frustrates Castiel to no end because he is also his current arch nemesis. 

Castiel still has trouble putting the Dean he met at his shop together with the Dean he argued with at the party. It’s almost like the guy has a split personality. How can he be so sweet and charming one minute and so vile and heartless the next? Castiel isn’t eager to find out and takes to the ridiculous methods of crouching behind displays and peeking around corners to avoid him. Castiel is almost in the clear when he makes it out the front door with his bags only to lose his grip on one and watch in dismay as a few cans and a bag of baby potatoes hit the sidewalk. He crouches down to pick them up quickly when suddenly someone else is right in front of him, grabbing the groceries before they roll away.

“Hey, Cas. Sorry if I startled you,” Dean says, a weary smile on his face.

“No, it’s fine. Just didn’t uh, realize you were here. Um, hi,” Castiel manages while grabbing the now-rescued groceries from Dean’s hands.

“Yeah, I saw you going through the store, seemed like you were trying to avoid someone,” he says with a cheeky grin. Castiel wants to be mad, but he is too ashamed of his childish behavior.

“Oh, no. Not me. Never,” he says sheepishly.

“Haha, right.” Dean’s grin is more sure now. “I just figured I would wish you a happy Thanksgiving since I saw you. I hope you’ve been doing well.”

“Yes, thank you. Happy Thanksgiving to you, too. I’ve been good. We’ve all been good. Me and everyone at the shop.” Castiel can feel himself getting defensive and tries to stop rambling.

“I’m glad to hear it,” Dean smiles a seemingly genuine grin despite Castiel’s standoffish demeanor. “I’m just heading off to my family’s big Thanksgiving dinner. It is quite the event, as you can imagine, with lots of young aunts and brothers and tree spirits to entertain.” 

Castiel lets out a huff of a laugh despite himself. Is Castiel seriously falling for his charm again? Castiel tells himself to get a grip, but Dean let’s out a big laugh and it makes it that much harder. 

“Well, have a good holiday, and take care.”

“Oh, right. Yes, you too,” Dean says, taking a step back out of his personal space. “Off to meet with family?” 

“Well, not exactly. Found family more than blood family.” Castiel shrugs.

“What do you mean?”

“I have Thanksgiving plans with my friends and coworkers. Most of us don’t have much family in the area, or don’t have good ties with them. So we make our own traditions.”

“Wow, that sounds a lot nicer than putting up with most of the people I’m going to see,” Dean laughs, but Castiel can see a bit of sadness in his eyes. “At any rate, take care, Cas.”

“You too, Dean.”

They part ways. Castiel is surprised that there was no bloodshed or cruel words thrown about. He supposes that there is plenty more time for that when the plans they have been making for the shop with Frank’s help are set in motion. But for now, Castiel is just reminded of the first time he met Dean.


	8. Put Up a Good Fight

Once Frank writes the article about the store, it is just a matter of letting Claire run with her idea of a rally to get things moving. The rally leads to more press and more press leads to more opportunities for Castiel to talk about the shop and why he loves it. Talking to large crowds and being on camera are not things that he is used to, but talking about The Shop at the End of the Universe comes easy to him. He can talk about his love for books and the neighborhood. He can talk about his father and growing up at the shop. He can talk about why small, independent stores are so important. Sure, it is tiresome and stressful, but if it makes a difference, Castiel is willing to push through. And yet, he can’t help the nagging feeling in the back of his mind that all these efforts might be futile.

Message from user – bookshop-boy, Dec. 8th,

_It is settling into winter, and it may be a cliché, but it always makes me a little sad and nostalgic. Do you ever wonder how long our parents thought about what our lives would be like? Do you ever wonder if their hopes for us were just generally good, or were they specific? Did they have something in mind as they tried to raise us to be specific people? I know my father had a lot of passion and he instilled that in me. He taught me a lot of things about running the business and about how to write, but I don’t remember him ever telling me that I could end up somewhere else besides where I am now. He talked about so many possibilities with creativity and exploration, but they were always within the parameters of the life he was already living. I feel a bit lost. I sort of fell into what I do now. I never thought much about doing anything else. That’s probably because I enjoy it, but I don’t know if I’m going to be able to do it much longer. Not by my choice, but by circumstance. I’m pushing myself more than I ever have to keep my life the way it is now, but I don’t know if it will be enough. And if it is not, then how will I know what to do next?_

Message from user – NY1967, Dec. 10th:

_It sounds like you need advice, and usually that is my specialty. Unfortunately, we have parallel problems. You may have had a much different kind of dad than I do, but we have ended up in similar situations. My dad has been grooming me to take over the family business since before I was born. I know for a fact that he always had plans for me. Luckily I’m good at what I do, so I could keep doing it forever, I guess. I’ve tried to think about what else I could do, but nothing ever seems right or plausible. Maybe you are lucky in that these circumstances, although they sound stressful, can be the push you need to dream about what else you could do. I never really liked that stupid saying of “when God closes a door, he opens a window.” It always made me cringe when people would say it because it is so cheesy and entirely unhelpful in a real crisis. But from what it sounds like, it may apply to your life right now. I wish you good luck my friend. I know you worry about being brave. But I already know you are brave. Fight for what matters to you. That’s all you can really do._

“I saw that piece the local news did on our competition earlier this week,” Charlie says cautiously after they have placed their order with the waitress.

“Ugh! Don’t remind me,” Dean rolls his eyes and settles further back into his seat. “We really got the raw deal on that one. Figures they would take his side. Keeps the drama alive, and people like to pretend they would support someone like him instead of us. In the end, they just want what they want as cheap and fast as they can get it.”

“I was surprised they got you on camera saying those things. I mean, sure, the press can be sneaky and editing was a huge part of it; but I can’t help but notice that you seem off your game a little lately. I’m surprised that this guy and his shop are still causing so much trouble for you.” 

Dean takes a deep breath and sighs.

“Honestly, you and me both,” Dean chuckles a little to himself. He should be more upset, and he is certain that an official ream session from his father is not far away, but he’s got to admit that he is surprised how well the guy is fighting back. Certainly not what Dean expected when they had their confrontation at the book party. “I thought I had a decent read on Cas, but I guess I underestimated him and his friends.”

“Hmmm, so it’s ‘Cas’ now, huh?” Charlies says with a teasing grin.

“Oh come on, Charlie. It’s nothing like… like that… whatever it is you are insinuating. Wait, what _are _you insinuating?” Dean narrows his eyes and cocks his head in confusion.

“Nothing, nothing,” Charlie holds her hands up in innocence. “Nothing particular, just that you might feel for this guy. You’ve been a bit more resistant to your father’s ideologies lately. Maybe you caught some sympathy.”

“Granted, you out of anyone know that I’ve been struggling with following all of my father’s orders, but the only feeling I have about Castiel is light annoyance.”

“Then perhaps it is a completely unrelated distraction?” Charlie asks hopefully.

“What are you getting at, kid?”

“Well, you just said yourself that you’ve been thinking differently than you used to. Now, I know that while I may question the status quo more often than most, I keep my head down and work for the greater good of my wallet and freedom. And this has always been my way, so it is clearly not my influence that is changing you. So it has to be coming from somewhere or some_one_ else. So, spill,” Charlie prompts as she props her elbows on the table and rests her chin on her hands.

Dean attempts to stare her down, but he has known Charlie for far too long to think that this tenacious woman would ever give up if she had even the slightest inkling of something juicy.

“Okay, but before I tell you, I just want to preface this with the fact that it’s not a big deal and don’t read too much into it.” Charlie is practically bouncing out of her seat. Dean takes another deep breath. “So, for the last few years I’ve been indulging in… in a certain social media site.”

“Instagram?”

“Nope.”

“Fetlife?” Charlie offers quickly.

“What? No!” Dean shakes his head.

“Oh no, my dear handmaiden. Have you fallen into the depths of Reddit?” Charlie asks with what looks like genuine concern on her face.

“No. I’ve, um, fallen into the depths of Tumblr.” Dean admits.

“Oh, Dean,” Charlie sighs. “Dean, Dean, Dean,” she says, shaking her head slowly from side to side. Dean cringes to himself as he waits for her judgement. “How?! How could you hide this from me? You know that I am the queen of fandom! Why wouldn’t you just tell me?”

“I’m sorry. I just wanted to keep it to myself. It was mostly an escape.”

“Whatever. Maybe I’ll forgive you if you tell me what this has to do with your distraction lately.”

When Dean hesitates Charlie begins to pout. 

“Fine, ya big manipulative baby.” Charlie beams at him and leans in for the story. “I kind of accidentally made a friend on there. And we’ve been talking a lot lately. I know that they live in the city, but I don’t know their name.”

“Is this friend just a friend, or are you going behind Patricia’s back?”

“No, no. Just a friend. Really. I wouldn’t do that to her.”

“Okay, if you say so. I guess I’m just glad that I have confirmation that I’m not your only friend in the whole world. It takes a lot of the pressure off,” Charlie teases and Dean rolls his eyes.

“Yeah, well. It isn’t real. I only know them online.”

“Oh, please. That totally counts! There are plenty of people I consider friends that I’ve never met IRL. How often do you talk to this friend?”

“It’s getting to be almost every day lately.”

“Well, dang. That’s almost realer than us! I would be jealous if I didn’t know that you’re hopelessly in love with me and would never survive without me.”

“Well, of course, my dear queen. No one comes before you,” Dean smirks.

“Damn right,” Charlie nods matter-of-factly as their food arrives.

Castiel makes his way into the back office of the shop and sits down next to Birdie. He is about to ask her something when they hear Gabriel announcing his plans to his coworkers. 

“Got myself a hot date tonight, so I’ll be stopping by the fancy soap shop to grab those artisanal candles to make my apartment smell mossy,” he brags. 

Castiel and Birdie share exasperated looks. 

“And I can’t decide if I should make my usual pork or try the new pasta dish I read about. Either way, we probably will get too distracted to eat,” Gabriel adds as he makes his way out the door to leave.

Castiel rolls his eyes.

“So tell me,” Castiel turns back to Birdie at the computer. Birdie simply shakes her head. “Seriously? Not any difference? How can that be? We’ve been doing everything we can.”

“I know, dear,” Birdie gently pats his forearm with her hand. “But we just simply aren’t getting the kind of sales we need this time of year. We all know you’ve been fighting as much as you can.” Castiel sighs and collects his thoughts.

“What do you think dad would have done?”

“Your father was a great man, but he wasn’t much of a businessman,” Birdie says carefully, eliciting a knowing smile from Castiel. “He was more interested in writing stories, and the shop was a consistent venture to fuel his creative endeavors. He loved it, sure, but he loved many things more. Like you,” she says, stroking Castiel’s cheek as he stares down at his hands in his lap. “I don’t think he would have known what to do in this situation. But I do know that he would say that your Butterbeer recipe is near perfection.” 

Castiel lets out a small laugh.

“Thank you, Birdie.”

“Goodnight, dear. I’ll see you tomorrow.”

Message from user – NY1967, Dec. 13th,

_I’ve been working hard lately, and I feel like I’ve been spinning my wheels. I really value the friendship we have created here. I don’t want to compromise that, but I would feel like a fool if I never asked. Would you be willing to meet me in person? Nothing too crazy, just for coffee or something. If you don’t want to, I understand. No explanation needed._

Message from user – bookshop-boy, Dec. 14th,

_ I value our friendship as well. I’ve been finding it more and more difficult to stick to our code of no specifics because I feel like I know you so well already. Yes. I would be happy to meet with you for coffee. How about Thursday evening at the café on W. 3__rd__ and Mercer? I’ll have a copy of the first _Supernatural _book on the table at 7 p.m. I’m looking forward to it._


	9. The Café

“So what’s the story, Dean?” Charlie huffs as they make their way down the sidewalk in the brisk early night air. “You drag me away from my luxurious plans of reading fan fiction in bed to walk you to some random café and now you tell me that I’m not even invited in?” 

“Okay, yeah, sorry. It’s just… I knew I couldn’t do this alone. It is way too tempting to just run the other way,” Dean’s voice is higher than normal, and he hopes it gets better soon.

“What do you mean? What are you planning to do at this café?” Charlie stops dead on the sidewalk and Dean shuffles her over to the side to let people pass before they create a pile up.

“Okay, fine,” he sighs as he runs a hand down his face. “Do you remember the friend I told you about? The one I’ve been talking to on Tumblr?”

“Of course, yeah.”

“Well,” Dean rubs the back of his neck with his hand. “We are meeting here tonight for the first time.”

“Oh, cool! Hey, that’s great. Why are you so nervous?”

“I, um… I just – “ Dean tries to gesture vaguely with his hands.

“If you are feeling anxious I can always just join you. It could be fun, and I could be your buffer if things get awkward. I’m great at meeting new people and keeping the conversation going.”

“That’s really sweet, Charlie. But I really need to meet them on my own. Because I think… well, I think that they may eventually, maybe, possibly, become more than my… friend.”

Once Dean finally spits it out, he feels a swoop through his belly. He has barely admitted to himself that he thinks bookshop-boy, or whatever his real name is, could be someone really special in his life. Now he has said it out loud to someone else, the realness of is all is almost too much to take.

“Wow! That’s really cool and all, but what about Patricia?”

“Patricia is… she’s fine. She and I have a lot in common and we get along. But she wants a certain type of life, and I’m just really not sure I want the same. That’s why I have to meet this guy and figure it out.” Dean claps a hand over his mouth as he sees Charlie’s eyes grow huge.

“This guy? Wait, you’re telling me that you know your friend is a guy and you think you may want to be more than friends?” Charlie hands are motioning wildly.

“Yeah, I guess. I don’t know,” Dean lets out a long breath and shakes his head, trying to clear it. “This is the first guy I have ever had any real romantic feelings for. I’m sorry I didn’t tell you, but I’ve literally told no one that I like men. Well, minus this guy...” Dean is afraid to look up at her. Charlie has always been open about her sexuality to Dean. He knows that she is the most obvious person in his life to accept him coming out, but it still feels scary to say the words out loud.

Charlie is smiling at him from ear to ear.

“How long have you known?” 

“Probably around middle school. I started noticing girls were cute around the same time I started noticing that boys were cute, too, I guess. I always figured that since I liked girls, I could just make that work. I mean, you know my dad. I always just pushed it down and ignored it because it made our relationship easier. But this guy… Honestly Charlie, if this guy is even half as great as I imagine him to be from our messages, I might just ask him to move in with me.”

“Hey, man,” Charlie points a finger in his face. “That’s our move! Lesbian’s have got the corner on that market for moving in too fast, so back off.”

Dean throws his head back in a laugh, releasing some of the tension in his shoulders.

“Okay, fine. I’ll cool it. But you got to do something for me.”

“Anything, my bisexual brother,” she answers with a proud smirk, forcing Dean to hold back a giggle.

“You gotta go check in the window and just tell me what he looks like. I need to know that he is there so I don’t wander in and look like a fool searching for him.”

“Okay, yeah, I got you. How do I know which one he is?”

“He will have a copy of the first book in the Supernatural series on his table.”

“Dude. Tumblr got you good, man. That’s almost too geeky for me.”

“Whatever, just do it, please.”

“Alright, alright.” Charlie walks over to the large window at the front of the café. She peers inside and searches out the mystery man. She suddenly puts her hand to her chest before she turns and exclaims, “Oh. Oh, wow. Okay, I know I’m a lesbian, but this guy is seriously about to turn me. He is downright gorgeous!”

“Seriously? Are you kidding me?” Dean asks excitedly.

“Yep! Sorry, I don’t see him yet.”

“Damn it Charlie! Don’t play me like this. I’m too nervous!”

“Okay, sorry. I’ll look for real, hang on.” Charlie giggles and goes back to searching the café in earnest. “Oh, okay. I see the book. The waiter is in the way, just one sec…”

“Well? What does he look like?”

Charlie spots a man sitting in the café in a tan trench coat sipping a steaming mug of tea. His dark hair is slightly untamed and his skin is quite tan despite the time of year. It takes her just a moment to realize why he looks so familiar and her face falls. She turns back to Dean and tries to find the words.

“What is it? Is something wrong?”

“I don’t know. Um, tell me, would you be attracted to someone who looks like, um, looks like that Castiel guy?”

“Castiel Shurley from the book shop? I mean, yeah. Cas is a good looking guy for someone who hates my guts. Why? Is that what he looks like?”

“You could say that. You could also say…that he _is_ Castiel Shurley from the book shop.”

Dean’s eyebrows furrow and he jumps up beside Charlie at the window to look inside. There, sitting at a two-topper with his Supernatural book, waiting for a companion, is Castiel. 

Dean just stares, dumbfounded and at a loss for words. He has enough sense to move back away from the window before Castiel spots him and Charlie follows.

“What are you going to do?”

“I… I don’t know. I can’t go in there. I mean – I mean, that guy hates me. That guy hates my family. Two minutes ago, I was thinking about us moving in together and coming out to my dad, but now… I can’t do that.”

“But Dean, you’ve built a relationship with this guy,” Charlie places her hands on his shoulders, rooting him to the spot before he can make a break for it. “You have been talking to each other for years. You don’t think that when he realizes who you’ve been to him, that he can get over who your family is?”

“Even if he could, my dad would never accept it. He would think I was trying to humiliate him or something.”

“Maybe so, but how much of your life are you willing to let your dad control?”

Dean doesn’t have an answer for that.

  
  


Inside the café, Castiel slowly sips his tea and tries not to burn a hole through the door with his stare alone. He had given himself a little pep talk before leaving for this meeting. He knows that despite the fact that he has feelings for NY1967, he cannot rationally expect those feelings will be returned. He has to be prepared for this meeting to end in friendship. That would be enough for Castiel. He hopes there will be more, but friendship is always worthwhile.

Castiel repositions the book on the table, making sure it is easily visible to anyone walking in. He glances back up at the door and his heart sinks. In walks the very last person he wanted to see tonight – Dean Winchester. 

It is bad enough that this guy is the reason Castiel’s shop is on the verge of closing, but tonight was supposed to be fun and exciting. Dean is at the counter ordering something, so Castiel grabs the book off the end of his table and opens it to a random page, burying his face in it to try to avoid being spotted by Dean. It doesn’t work.

“Oh, hey Cas. Fancy meeting you here,” Dean says as he approaches the table. Castiel could swear that he senses a bit of nervousness in the man’s voice, but he quickly dismisses it. “Is this seat taken?”

“Yes!” he exclaims as he reaches over to pull the chair back in. “Yes, actually, it is. I’m expecting someone. So, if you wouldn’t mind just leaving me be. I’ve spent quite enough time thinking about you lately, and I would like to enjoy my night.”

“Been thinking about me, huh?” Dean asks with a smirk.

“You know what I mean,” he says as he fixes Dean with an icy glare. “I’ve wasted enough of my energy fighting your store, so please, just go away.” 

Dean grabs his coffee off the counter when it is done and moves to sit at the table directly across from Castiel.

“Seriously?” Castiel says with a huff.

“What? I’m just going to enjoy my coffee. I won’t bother you,” he adds as he takes a tentative sip from the steaming mug.

“Fine,” Castiel sighs as he reopens the book and tries to read while continuing to glance back at the front door.

“That’s your father’s book, right?”

“I thought you were not going to bother me,” Castiel states into the pages of the book.

“I’m not trying to. I just wanted to talk to you about it. I read it after I bought it from your shop. It was good. Fun, frightening. He was a good writer.”

“Thank you, but I don’t need you to tell me that.”

“I’m just trying to be friendly. I’m a really decent person once you get to know me. I think you would discover a lot of things if you really knew me.”

Castiel turns to look him in the eye directly, completely fed up with his nonsense and distraction. “If I really knew you, you know what I would find? Instead of a brain – a cash register, and instead of a heart – a bottom-line.” 

Dean’s face falls just as Castiel’s lights up.

“I’ve just had a breakthrough.”

“Oh, yeah?” Dean asks, taking another sip of his coffee.

“Yes. For the first time in my life, I have been confronted by a person and instead of getting flustered, I have said exactly what I wanted to say at the exact moment I want to say it.”

“Well, you certainly have a knack for it. That was the perfect combination of poetry and meanness,” Dean admits quietly. Castiel’s smile waivers. “I’ll just give you some more space.” 

Dean gets up and takes his coffee and sits at the table directly behind Castiel. Castiel rolls his eyes, but he places the book back on the table and tries to refocus. The front door opens and in walks two older women and Castiel can’t stop the slump to his shoulders.

“So, are you meeting someone special tonight?”

“I thought you were going to leave me alone,” Castile responds with more sadness in this voice that he can’t hide.

“I’m just curious. Is it someone you know, or someone new?”

“Will you leave me alone if I tell you?”

“Possibly. No way to tell until you do,” Dean teases.

“The person I’m meeting tonight is a wonderful man who is smart and funny and honest. Something you don’t know anything about.”

“I was always honest with you. I never lied.”

“Oh really,” Castiel accuses, turning in his seat to confront Dean directly. “’Dean, just call me Dean’? Who do you think you are, Cher? You knew that if you told me who you were, I wouldn’t have talked to you like I did. I wouldn’t have talked about the shop or my father.” 

Dean gets up and returns to Castiel’s table to face him head on.

“I told you before, I just wanted a nice afternoon out with my family. Sometimes it is nice to not have all of the baggage attached to me that comes along with my last name.”

“Oh you poor, sad multi-millionaire. Life must be so difficult for you,” Castiel mocks, the heat returning to his voice. “You may have deluded yourself into thinking that you can separate yourself from your actions, but in the end you are a willing cog in that machine. And although you are successful now, nothing lasts in this economy. Someone will come along and have a better idea with tighter profit margins and faster service and then no one will remember you. And maybe no one will remember me either, but plenty of people remember my father. He was a kind man who wrote stories that people loved. You, Dean Winchester, are nothing but a suit.” Castiel sits back in his chair, breath quicker than normal, but his stare unwavering.

Dean slowly smooths his hands over the table between them. “Well, I guess that’s my cue,” he says as he stands up and gathers his coat. “You have a nice evening.” 

He makes his way out the door, leaving Castiel alone at his table with the determination draining from his face.


	10. He Stood You Up?

Castiel allowed himself to wait a full hour past the agreed meeting time. After Dean Winchester had left, he told himself that he wouldn’t give up until then. His legs felt heavy when he walked out. He told himself that he wouldn’t obsessively check his messages all night. He let himself check just once when he got home. Nothing from NY1967. Castiel went to bed and promised himself he wouldn’t lose sleep over this guy.

The next morning, he was inside the shop for less than thirty seconds before Claire confronts him at the register counter. 

“So?” she asks with excitement in her eyes, something rarely seen in the usually acerbic young woman.

“So, what?” Castiel responds, trying to appear too busy to indulge her.

“Sooo... what happened with mystery man?”

“He, um,” Castiel pauses, fiddling with papers behind the counter, “he couldn’t make it.”

“He stood you up?” she exclaims. Claire almost sounds more disappointed than Castiel.

“No, no. I’m sure something came up. It’s not like he owes me anything anyway.”

“Yeah, I guess. But it still sucks,” Claire offers.

Castiel continues to seem busy behind the counter as Claire ruminates in front of him before she says, “I mean, there are probably a million different reasons that he couldn’t make it.” Castiel finally looks up at her. “I had a date cancel once because he sprained his ankle playing catch with his nephew earlier the same day.”

Castiel nods, following along her way of thinking, “I mean, you’re right. He could have been injured or... or maybe he was in an accident.”

“Yeah, maybe he was hit by a cab. Just crossing the street in this city can be like taking your own life in your hands.”

“Right!” he gestures emphatically. “And it’s not like he could call or text me, he doesn’t have my number. Maybe his phone was smashed in the accident.” 

Castiel is almost feeling better with this wild tale when Gabriel walks in through the door with a coffee cup in hand and a newspaper under his arm.

“Hey! So what happened with that guy?” he asks as he comes up to the counter.

“We think something happened to him, possibly he’s in a coma,” Claire says.

“He stood you up?” Gabriel exclaims. Castiel groans as he throws his head back and turns away. “What? What did I say?” he asks turning between Claire’s annoyed face and Castiel’s back.

“Listen, this is just a sign. I was getting ahead of myself thinking that this was supposed to be some kind of date. Besides, I already have someone in my life.”

“Who?” Gabriel asks.

“Frank, of course!” Castiel huffs as he turns back around.

“Ohh, yeah. Right,” Gabriel nods absentmindedly, placing his items on the counter.

“At any rate, something clearly happened that prevented my friend from showing up last night. I’ll probably get an explanation soon,” Castiel says, trying to wrap up the discussion.

“Or…” Gabriel starts.

“… or what?” Claire asks.

“Or, he couldn’t make it because he was in jail!” he crescendos, holding up the paper he brought in. On the front page was an article about the arrest of the “Rooftop Strangler”. “This guy was arrested just a few blocks from the café!”

“Oh my god!” Claire grabs the paper from Gabriel’s hand.

“He didn’t show up because he was in jail!” Gabriel announces.

“No! That’s crazy. He’s not the Rooftop Strangler!” Castiel shakes his head at how ridiculous this thought experiment has become.

“You say that, but it would definitely explain why he didn’t show last night,” Gabriel says with a conspiratorial raise of his eyebrows. 

Luckily Birdie walks in before Castiel has to answer that ludicrous accusation.

“So…” Birdie asks with hopeful mirth, “tell me how it went!”.

“He was unable to make it,” Castiel answers simply.

“He stood you up?” 

Castiel lets out an undignified groan and turns away.

  
  


Message from user – bookshop-boy, Dec. 18th:

_I’ve been thinking about you lately. I don’t know what happened to you the other night, and maybe I never will. But you’ve become a significant person in my life, and it would be even sadder if one missed meeting ended that. _

_ I miss you. When I was waiting for you at the café, someone else from my life showed up; a man who’s made my professional life a living hell. He was the last person I wanted to see, but I had a breakthrough. I finally achieved my dream of saying the exact thing I wanted to say the moment I wanted to say it. And you were right – instant regret. I was cruel, and I’m never cruel. And although it probably didn’t even affect this man in the slightest, the guilt soon followed. He’s probably not the type to get hurt by the words of someone like me, but that is no excuse for me to behave like I did. _

_ I don’t think I’m cut out for a type of life that brings me to contentious blows like my current situation does. I just wish I could talk to you. This form of communication means you’re more likely to talk about nothing than something. Such is the price we pay for low stakes, high volume social media. But I just want to say that all of our “nothings” have meant more to me than so many other “somethings.” So thank you. And I hope to hear from you again soon._

  
  


“Dude! What happened to you last night?” Charlie exclaims as Dean enters their usual bagel shop. He knew this was coming, but that doesn’t mean he is any more ready to take on this conversation. “I was waiting up to hear from you, but you went silent,” 

“It, uh, did not go well,” Dean eases into the story as he flops into the chair across from his best friend. “He wasn’t thrilled to see me, to say the least. We argued and he told me off. He gave me every indication that he has no interest in seeing me again unless he was picking me out of a police lineup.”

“Wow. That sucks,” Charlie cringes and Dean huffs out a dry laugh.

“Yeah, well. Clearly the guy is completely wrong for me anyway. My family would have thought I was nuts, and they would be right. He has no interest in someone with my life, and that’s just fine. I’ve got a great life, so if he doesn’t want a part of it, that’s his loss,” Dean says matter-of-factly to a blank faced Charlie. “Besides, I’ve got Patricia. She fits in great with my family. It’s a good match.”

“Huh,” she says dryly.

“What?”

“Nothing.”

“No ‘nothing’. What do you mean by ‘huh’?” Dean asks, getting agitated.

“It’s just… is that a reason to be with someone? Because your family likes her?” Dean throws his hands up in confusion at Charlie. “I mean sure, it’s better than trying to date someone your family hates,” she adds quickly. “But in the end, they aren’t dating her: you are. Shouldn’t you be with someone that makes _you _happy and excited?”

“Patricia does make me happy. And she understands my life better than most people. She gets it,” Dean remarks decidedly.

“Okay, dude. I just want you to be happy.”

“Well, I am,” he adds with a curt nod.

  
  


That night, Dean finally allows himself to check his messages. He has been avoiding his account since the incident at the café. He didn’t want to face what bookshop-boy had to say about him never showing up. Well, really him _thinking_ that he never showed up.

Castiel’s message hits him hard. Dean reads it at least three times, letting it sink in. Dean never imagined that their argument at the café would affect Cas like it did. 

Dean feels guilty for being the cause of Castiel’s guilt, which made him feel ridiculous on top of that. Here’s a guy whose family business is failing because of him, and he can’t even handle telling him off without feeling bad about it. Castiel is too kind for the likes of Dean, that’s for sure. 

Before he sends himself into a self-deprecating tail spin, he decides that he can’t just leave Castiel like this. They guy at least deserves to not be ghosted

First Dean tries a few lies. Maybe he can make up a decent enough excuse for missing the meeting to spare Castiel’ feelings. Maybe Dean was stuck in a meeting and the power went out. Maybe his phone died or there was no signal. Or maybe the subway broke down and he was trapped underground. Maybe he had to fly out of town last minute because of… a sick aunt?

Dean shakes his head to himself and deletes yet another attempt at his message to Castiel. He knows he shouldn’t lie to the guy, not anymore. He already made him sit through one terrible evening while holding back the truth. 

But Dean doesn’t want to reveal who he is just because he knows for sure that Castiel would cut off all contact. Castiel may feel bad about what he said, but he still doesn’t like the Dean Winchester he knows in real life.

Message from user – NY1967, Dec. 19th:

_I’m so sorry for what happened. You were expecting to see a friendly face, and instead you had to deal with someone who brings you pain. I’m sure that what you said that night was provoked and deserved. That doesn’t change the fact that it left you feeling guilty and sad. The fault is mine. You have become a significant person in my life as well. Someday I’ll explain everything. Until then, I’m still here. Talk to me._


	11. But We are So Perfect for Each Other

Birdie lives in a comfy old brownstone that is full of overstuffed couches covered in throw pillows and soft blankets. Castiel has never figured out how she came to live there, much less afford to stay for so many years. He has his suspicions that she used to be someone’s kept woman, and they eventually left the place to her. 

Castiel has been having tea at Birdie’s place since he was about 9 years old. She always has shortbread cookies, sometimes spiced with cardamom, and dozens of mismatched tea cups to choose from. When Claire began working at the shop, she got invited to join as well. Birdie hosts tea about once per month. 

Gabriel got invited once, but he ate the entire tray of cookies and brandy snaps before the tea even had time to steep. He hasn’t been invited back. 

Often, Birdie takes the time to tell old stories or talk about new books. Today is a more somber occasion.

“So, you’ve decided then?” Birdie asks when they are all seated around her glass-topped kitchen table.

“Yes. We are going to close,” Castiel replies, nodding his head solemnly. “It was a tough decision, but it has to be done.”

“How long do you think?” Claire asks, already prepared for the announcement despite her enthusiasm for the fight these last few weeks.

“A month, maybe less,” Castiel sighs. “We will have a sale to get rid of the rest of the inventory and some of the fixtures and various items. We just didn’t get the sales we needed through the holidays. I imagine it will be done by the start of February.”

“Well, you may not believe me when I say it, but I’m proud of you,” Birdie says, patting his hand that rests on the table top.

“What do you mean?” Castiel scoffs. “I gave up.”

“Yes, but not without a fight,” Birdie argues. Castiel smiles quietly and sips his tea. “You may feel like a failure, but it is a very brave thing you are doing. You are daring to imagine that you could have a different life.” Claire nods along with the sentiment.

“I just wish I knew what that life was,” Castiel laughs.

“You’ll figure it out. You’re a smart young man. You have a lot to offer the world beyond the book shop. I look forward to seeing how it all plays out.”

“You and me both,” Castiel adds, getting a short laugh from Claire.

“Well, until then you will just have to explore your options. Have you still been talking to that man on the internet?”

“Yes, we still talk,” Castiel states simply, taking another sip from his mug.

“Did he ever tell you what happened?” Claire asks.

“No, but it hasn’t really changed things. We still chat about everything and nothing.” Castiel looks from Claire to Birdie with soft eyes. “It is nice to have as many friends as I can get right now.”

“And what about you and Frank. How are you two doing?” Birdie asks.

“Oh, fine, I guess. He’s been busy lately, and so have I. We haven’t seen each other much, but it doesn’t seem to be affecting us. We have dinner plans tonight, I think.”

“You know, I’ve been blessed with a few great loves during my life,” Birdie starts, a wistful look in her eye that piques Claire’s interest immediately. “Most of them were very passionate, but they fizzled quite quickly. Perhaps the love you and Frank have is more enduring. You two don’t seem to have so much a fire but a slow warmth.”

“I guess, yeah. I’ve definitely never felt anything like fire with us, but it is comfortable and supportive.”

“That’s nice, dear,” Birdie smiles and takes another cookie from the platter.

  
  


“Hey, Frank, can I ask you something?” Castiel opens with once they are seated at the restaurant and looking over the menus.

“Sure,” Frank replies, not looking up yet.

“Are you happy in our relationship?” Frank looks up now, eyebrows furrowed. “I know we don’t fight, and I enjoy your company. You’re very smart and passionate about a lot of things, but one thing neither of us has been particularly passionate about is, well – our relationship.”

“Do you… do you have doubts about us?” Frank asks, seemingly testing the waters.

“I don’t doubt that we have a nice relationship, but I just…” Castiel searches the space above Frank’s head as if it will provide him with the right words. “I’m really sorry to say this, but I feel like I love you, but I’m not in love with you.”

“Oh. Wow,” Frank stalls for a moment as Castiel’s stomach turns. “It’s funny, because I feel the exact same.”

Castiel shakes his head in disbelief. He lets out a short laugh and then Frank breaks into a smile. 

“Really?” Castiel asks, leaning back in towards Frank.

“Yeah! I think I’ve been too afraid to say anything, especially with the shop trouble and all, but yeah.” Frank sounds relieved and Castiel’s stomach stops flipping.

Castiel takes a moment to let it sink in. “But we are so perfect for each other,” he muses, leaning in almost conspiratorially.

“I know!” Frank exclaims as he and Castiel share a laugh.

“Well, okay then. That was easier than I thought.” Castiel settles back in his chair and looks over at his now ex-boyfriend. “So, is there anyone else? Someone you’ve been thinking about?”

“There is actually this one guy…”

“Ooo, do tell,” Castiel leans in with an exaggerated arch of his brow, genuinely interested in Frank’s future happiness.

“Well, I met him when I was doing interviews for a piece about some of the big players on Wall Street.”

“Oh Frank,” Castiel pretends to mock him, “is he a republican?”

“You know, I just can’t help myself,” Frank says with glee, instigating another fit of giggles. “What about you?”

Castiel shakes his head slowly. “No. No one in particular. But there is the dream of someone.”

  
  


The going out of business sale is more emotional than Castiel expected. The shop is packed with people. Most are just looking for a good deal, but many of them are long-time customers wanting to offer their condolences or express their anger over the shop closing. Castiel tries to smile and nod through it all, but it is much more draining than he thought it would be. Which is why he can’t explain what makes him walk into the Winchester Books Superstore one night. 

Castiel is surprised how large the place feels inside. It is full of people, but still relatively quiet. He wanders from section to section, often tempted to pick up a book and read the back. He is walking through the sci-fi section when he is approached by a woman with fiery red hair. 

“Good evening. Are you finding everything you need?”

“Oh, yes. I’m fine,” Castiel answers quickly.

“I’m Charlie, by the way, and…” she steps a little closer and lowers her voice, “I don’t mean to make you uncomfortable, but I recognize you. You’re Castiel Shurley from the sci-fi book shop.”

Castiel schools his features and quickly puts the book he was looking at back on the shelf, having a strange feeling of guilt run through him despite himself. “Yes, but I’m not here to cause a scene or anything, I was just browsing. I can leave if you want me to,” Castiel takes the coat he had been holding in his arms and puts it back on.

“No, no, of course not. You’re fine here. I was just hoping that I could chat with you for a second.” 

Castiel was not prepared for something like this. “I mean, if you must. I don’t imagine there is much more to say. You all won. The shop is closing,” Castiel offers with a defeated tone.

He sees Charlie wince slightly. “Listen, I know you won’t believe me when I say this, but I’m sorry that this is happening to you. I’ve actually been to your store before, and I thought it was great.”

“Well, thank you for that, I guess,” Castiel forces a small smile.

“The reason I wanted to talk to you is… well, I know that you can’t stand this place or the people who run it. And that is certainly valid, but… I guess I just hope that one day, you can forgive us for the way it worked out.”

Castiel tilts his head to the side and furrows his brow, “What do you mean by ‘us’? The company?”

“Not exactly,” she chuckles nervously. “You see, my best friend is Dean Winchester.” Castiel clenches up and takes a step away from her. Charlie takes a step forward and puts her hands up in placation. “And I know that when he is fighting for his dad’s bottom-line, he can come off as a real jerk. But from what he has told me about you, I feel like you guys could have been friends. It is just such a bummer you had to meet like this.”

“Well, I’m sure that Dean is a good friend to you, and you can tell him that I’m sorry for the things I’ve said in anger, but right now, I can’t see us being friends,” Castiel concludes in a rush, gathering his coat closer to himself and backing further down the aisle. “Have a good evening.” 

Castiel turns to leave, but something at the end of the shelf catches his eye. On a display endcap is every single book in his father’s series. 

He is frozen in place. Castiel reaches out to touch them, some he hasn’t seen outside of his own apartment in years. The sign above the display invites patrons to explore a classic series from a local author. 

Charlie approaches him again and stands at his side. 

“Dean made sure that he got as many of the complete set as he could,” she states quietly. “He’s had the display up since we opened. It’s been doing well, especially for an older title.”

Castiel doesn’t know what to say. He just stands there, fingers lightly grazing the spines of each volume.


	12. If I Ever Get Out of Here

Patricia and Dean exit the cab and make their way inside their apartment building. She is talking to Dean about something to do with a new editor she has hired or fired. Dean isn’t sure which, but she seems annoyed about the whole thing. They go through the lobby to the elevator.

“Good evening, Mr. Winchester.”

“Hiya Garth. How’s the night been?” he asks the elevator operator.

“Not too bad.” 

They are followed onto the elevator by an older woman carrying her small Pomeranian, and then the doors slide shut to take them up to their apartments.

The elevator has only made it up a few flights when the lights flicker and it comes to a stop.

“What’s going on now?” Patricia asks, annoyance already flaring in her voice.

“I’m not sure. It must be stuck,” replies Garth with a trace of anxiety in his voice. 

Patricia lets out a frustrated grown and Dean sighs to himself. He picks up the emergency phone inside the access panel and calls for help. The operator at the other end of the line says that they are on their way, but he isn’t holding his breath that it will be quick this late on a Sunday night. 

“Maybe if we all jump up in the air at the same time, the elevator will think that there is no one is inside, and the doors will open,” offers Garth in what he must feel is a stroke of brilliance from the proud look on his face.

“Is that a thing?” Dean asks. Garth just shrugs his shoulders. Dean figures it won’t hurt to try. “Alright, everyone, on the count of three. One… Two… Three!” 

They all jump into the air and come back down. Nothing changes.

Forty-five minutes later, the four human occupants along with one small dog are seated on the floor of the elevator, trying to pass the time while they wait for help.

“You know,” starts Garth, mostly to himself, “If I ever get out of here. I’m going to ask Bess to marry me. I love her. I don’t know what I’ve been waiting for.” 

He pulls out his wallet and shows Dean a picture of a sweet looking, conservatively-dressed woman. Dean leans in and smiles politely at the photo.

“If I ever get out of here,” chimes in the older woman with the Pomeranian, “I’m going to start talking to my mom again. She deserves another chance.” 

Dean nods to her. He begins to reflect on his own regrets when Patricia cuts with a huff as she looks through her purse.

“If I ever get out of here, I’m going to have my eyes lasered,” she states in monotone as she continues to search her bag. Dean holds back his scoff.

“If I ever get out of here – “ Dean starts.

“Ugh! Where are my Tic Tacs?” exclaims a frustrated Patricia. Dean looks over to her with a raise of his eyebrows. 

“What?” she snaps back.

  
  


Message from user – NY1967, Jan 28th:

_ Have you ever had a moment in your life when you suddenly see someone for who they really are and you wonder how you could have missed it for so long? I got into an elevator last night with the woman I thought was the right person for me. An hour later, I got out of that elevator and I packed my things to move out. _

_ There was another man sitting in the elevator with us that knew exactly what he wanted in life. I found myself wishing I were him. There have been a lot of times recently where I have discovered that many of the things I do, I do because that is what I thought was expected of me. But with just the slightest analysis, suddenly none of these things makes sense anymore. My thoughts are fuzzy at the moment, further analysis is needed._

  
  


Message from user – bookshop-boy, Jan 30th:

_Change is difficult. I know, what a cliché, but it is true. And no matter how many times I have heard it before or experienced it myself, it always hits me hard. My store is closing this week. I don’t know if I ever told you that I own the store I work at, but I did. But now we are closing, and sometime next month it will be something really depressing – like a Baby Gap. _

_ And some foolish person will think it is a tribute to the city with some dismissive sentiment about how nothing stays the same. And maybe they have a point and maybe that can be a good thing. But right now I’m heart broken. I’ll be fine eventually, but until then, the sting is very real and I need to give myself time to heal. Our store was open for forty-two years between my father and me. I’m sure he would have found that fact to be some sort of poetic irony. I miss him more this week than I have in a long time._

  
  


Dean has been staying at his father’s old bachelor pad that he keeps for in-between wives. It is certainly convenient to have somewhere to crash while he looks for a new place, but it is a bit depressing in its single-dom. About two weeks after his break up with Patricia, Dean comes back to the apartment with groceries when he spots his father getting out of a cab in front of the building. He is pulling a duffle bag out of the trunk along with a rolling suitcase.

“Oh no,” Dean calls out to him. “Say it isn’t so.”

“You got room for one more?” John asks with a sheepish grin.

Inside the apartment, Dean pours his father a glass of his favorite whisky as he gets the details about his breakup with Bela.

“Well, at least I didn’t marry this one, so no alimony. But the apartment was hers, so I’ll have to go searching for something new. I gotta say, I didn’t see this one coming.”

“Well, she was quite young, dad. We millennials tend to be a bit flaky,” Dean jokes and gets a guffaw out of the older man.

“You’re right. It’s just usually my fault when these things fall apart. Besides your mother -- God rest her soul -- every relationship I’ve had has been personally deconstructed by yours truly.” 

Dean is surprised to hear his father talking so candidly. Usually, the only thing they talk about together is business. 

“After your mother, it was Theresa, the former model.”

“She was also my nanny,” Dean reminds him as he pours himself a glass.

“She was the nanny? Wow, isn’t that ironic.” John laughs to himself, but Dean isn’t sure why. “Then, after Theresa, there was Melanie, who gave me Sammy.”

“Also my nanny.”

“You’re kidding me! Well this is getting ridiculous,” John laughs and shakes his head. “Then the next one was, uh, Sandra, the ballerina.”

“One of Sammy’s nannies, I believe,” Dean adds as he comes to sit down next to his father.

“Well, the pattern is complete,” John laughs to himself.

Dean looks at him with a quirked eyebrow. “So you said Bela ran off with someone. Anyone you know?”

“I do,” John smiles as he takes a sip from his glass,” the nanny.”

“Nanny Donna?” Dean exclaims in genuine surprise. Quickly, he finds the humor he was missing and doesn’t hold back a laugh. “Well, well, well. Bela ran off with Nanny Donna. That really is ironic.”

“Well, nothing to be done about it now,” John gets up from the couch to grab himself some more ice. “Who did you say you broke up with?”

“Patricia. She was… well, she was just not right for me,” he states matter-of-factly.

“Would I like her?” 

Dean glares over at his father. 

“Just kidding, son,” John laughs as he comes back to sit down. Dean cracks a broad smile. It is nice to actually be having a fun conversation for once with his father. “Well, I guess we are both in the same boat, so to speak.”

“Yes. Do you plan to stay here long? I’ll be out of here soon, I think,” Dean assures him.

“Don’t worry about it. I just have to find someone new. That’s the easy part,” John muses as he swirls his glass.

“Oh yeah, a snap to find the one single person in the world who fills your heart with joy,” Dean says, his tone dripping with sarcasm. 

“Don’t be ridiculous, son,” John laughs. “Have I ever been with anyone who fit that description? Have you?”


	13. The Friendliest Flower

Castiel watches as David Venable on QVC gushes about how gorgeous the new bakeware from Temptations will look when you are hosting your next dinner party or backyard cookout. Castiel has never bought anything off the T.V. before, but the last segment with the chocolate popcorn mix was especially tempting. 

The cold he is fighting must really be going to his head because he is just about to get up to find his credit card when his door buzzer goes off. He makes his way to the intercom and presses the button. 

“Hello?” he croaks out. Even Castiel can admit that he sounds pitiful.

“Yeah, hi. It’s Dean Winchester.” Castiel takes a moment to process this information. Probably quite a long moment because Dean calls out again over the speaker. “Are you waiting for me to go away?”

“No, sorry. No. I’m just confused,” Castiel calls back quickly, shaking his head out of his slow musings. “What do you want?”

“Well, umm, I heard you were sick and I brought you something. Also, I was hoping to talk to you about something important. If you are feeling especially bad, it can wait, I guess.”

Castiel racks his brain to try to figure out what Dean Winchester could possibly want to talk to him about. Despite the general tiredness and constant runny nose, he isn’t feeling as bad as he was yesterday or the day before. He supposes he should just let Dean talk and get it over with. 

This conclusion must have taken a significantly long time to reach because by the time Castiel is reaching to hit the button to respond, there is a knock at his door that startles him a step back.

Castiel checks the peephole, and lo and behold, Dean Winchester is waiting outside with a folder under one arm and a bouquet of flowers in the other.

“Cas?” Dean calls through the door. “Someone let me in the front door. Can I come in?”

Castiel looks around the horrible mess that is his apartment and grabs the trash bin from the kitchen. “Just a second!” he calls through the door as he quickly grabs up all the used tissues. He gathers up his dirty plates and cups and hides them away in the sink. He goes back to the door to open it when he realizes he is wearing a t-shirt with a multitude of holes and his oldest pair of sleep pants. He grabs his trench coat from the closet and throws it on before he finally unlocks the front door and greets Dean.

“Hello, Dean,” he says, his voice even lower and more gravely than normal from the cold. 

“Heya, Cas. I, uh, brought you some flowers to cheer you up while you’re stuck inside getting better.” Dean holds up the bouquet with a sheepish smile. 

Castiel is almost annoyed at the kind gesture but decides to motion him inside the apartment anyway. Dean’s smile brightens and he steps into the living room.

“Um, how did you know that I was sick?” Castiel asks as he points to the couch for Dean to sit down, but Dean continues to move around the room a bit, his eyes wandering over Castiel’s space.

“Gabriel told me.”

“Oh, right. He told me he started working for you. How is that going?”

“Well, he is a character, that’s for sure,” he chuckles. “But he definitely knows his stuff.” 

Dean glances around the apartment, soaking in the details. It is filled with books, of course, but also some nice cozy furniture, a few good lamps, and more than a few tchotchkes that feature bees. He turns back to Cas. “Do you have a vase I can put these in?”

“Yeah, uh, in the kitchen on top of the fridge,” Castiel answers as he lets himself plop back on the couch. He hears Dean rummaging around the kitchen, setting up the flowers in their vase, filling it with water, throwing away the wrapping. 

Castiel isn’t sure how to feel about having Dean in his home. Ever since he went to Winchester Books and saw the display of his father’s series, Castiel has had some strange, mixed feelings about Dean. As the pain of closing the shop eases, the urge to hate Dean has begun to go with it, and Castiel is left in this space between wondering what is real about Dean and what is simply Castiel projecting onto him.

Dean comes back to the living room and places the flowers on the coffee table and Castiel smiles. 

“I love daisies. They just seem like the friendliest flower.”

“I know, that’s kind of why I’m here,” Dean says, rubbing his hands together in a nervous motion as he sits down in the chair off to Castiel’s side.

“What do you mean?”

“I was hoping that you and I could talk about some things. And I was also hoping that… well, that I could be your friend,” Dean states, trying to sound open and confident in his request.

“You?” Castiel’s brow furrows together.

“Yes?” Dean offers, hopeful and confused.

“You want to be my friend?”

“I really do.”

Castiel closes his eyes shakes his head a bit in confusion, “I’m sorry, but I have to ask. Why do you want to be my friend? Or actually – ,” he stops, putting his hand up between them, “Why do you think that you and I could be friends? You really don’t know much about me at all, and I feel like everything I know about you is somehow not real.” 

Dean nods to himself and seems to gather his wits before answering. “Well, there are really good answers to all those questions, but to explain it, I have to confess something to you, and I’m kind of afraid that you are going to be mad,” Dean states, not looking him in the eye and running his palms over his jean-clad thighs. “And despite the fact that you think you are no good at speaking your mind, in my experience, that hasn’t stopped you from getting your anger across loud and clear.”

“Oh, you mean that night at the café?” Castiel sighs and slumps his shoulders. “Listen, I’ve wanted to apologize about what I said for a long time. I was horrible to you.”

“Let me stop you,” Dean holds his finger up, looking back at Castiel’s face, “because there is no need to apologize. I was the horrible one. I still am, actually. But I want to change that.”

Castiel takes a brief moment to think before conceding and sitting further back on the couch. “Okay. Well, before my meds really kick in and I pass out on you, go ahead and tell me what you came to say.”

Dean looks exceptionally nervous. Castiel would find it endearing if he wasn’t just as nervous about hearing what Dean wants to tell him.

“That night at the café, when you were there to meet a friend, and I showed up...” Castiel nods for Dean to continue. “The thing is, the friend you were there to meet really did show up.”

“Wait, are you saying that you stopped me from meeting him? Did you talk to him and make him leave?” Castiel’s voice starts to get louder as he fills with anger and he leans forward.

“No, no, it’s nothing like that!” Dean placates, putting his hands up to gesture at Castiel to calm down. “Okay, I’ll just tell you. I’m – I’m him.”

Castiel stares at him and impatiently gestures for him to explain, because he has no idea what Dean is talking about at this point, and he is getting seriously annoyed. 

“I’m NY1967,” Dean says, taking in a breath.

Castiel is pretty sure that he has just had some sort of stroke. He tilts his head to the side in confusion and can’t think of any response to what Dean just said.

“You and I are already friends in a way, we just didn’t know it,” Dean tries to smile at Cas, but the other man’s expression remains the same. “Listen, I had no idea that you were bookshop-boy until that night when I showed up at the café and saw you sitting there with the book on your table. I didn’t know what to do. I thought,” he moves his hands in front of him, trying to get out the nervous energy, “I thought about just leaving. But that would have been too cowardly. I thought about owning up to it that night, but when we started talking it all went downhill so fast. You hated me so much that I got defensive and hid who I am.”

“So,” Castiel starts, finally finding his voice, “you’re telling me that the same person who has been building me up and helping with my stress and listening to my stories and making me feel like an amazing person is also the same guy who has been the cause of all of that stress the whole time?” he states slowly.

“I would call it ironic, but that seems wholly inadequate at this point,” Dean says, trying to lighten the mood.

“I – I don’t believe it. So, you – Dean Winchester – businessman extraordinaire and next in line for your family’s millions, is a secret Tumblr user with social justice and liberal tendencies and a serious LARPing addiction?” Castiel questions incredulously. “_The_ Dean Winchester,” he raises his voice emphatically, “is a bisexual nerd-boy who has written Harry Potter fanfiction as long as a full novel?” Dean isn’t sure if he is supposed to laugh or wince at Castiel’s disbelieving descriptions. 

“Yeah, well, I told you that I had good answers for why we could be friends,” Dean offers with little hope it will fix the trajectory this is going.

“I just, I need to process this,” Castiel stands up and begins to pace. “Because it’s not only that you and my best online friend are the same person, but you have known our connection for almost two months! Yet you still kept talking to me like nothing had changed.”

Dean rises up from the chair to get closer to Cas again, “You’re right. That’s where I need to apologize,” Dean starts, but he is interrupted by a coughing fit from Castiel. “Here, let me make you some tea and then maybe you will let me tell you why I – why I was such an asshole.” 

Castiel hasn’t quite caught his breath from coughing, but he nods at him. Dean takes this as permission to go ahead and make the tea and goes back into the kitchen. 

Dean stays in the kitchen while the water boils and he selects the tea bag and a mug. He is surprised that things have gone so well so far. He wasn’t even expecting to get through the door, let alone Cas being willing to listen to his explanation. Dean had practiced what he wanted to say a handful of times before he finally talked to Gabriel to find out how to see Castiel. 

Charlie had told him about Cas coming to the store. Dean was hoping that seeing what he had done would give him enough goodwill to get through revealing the truth. 

The tea kettle whistles and Dean pours hot water over the peppermint tea bag. He grabs a spoon and a jar of honey from the counter. He takes a deep breath before going back into the living room.

Castiel has taken off his trench coat and is now sitting cross-legged on the couch with a blanket over his lap. The shirt he is wearing is loose and shows off his sharp collar bones. Dean tries not to stare as he places the tea and honey down on the coffee table and goes back to his chair.

He waits for Castiel to take a timid sip before he takes another deep breath. “I want to start by saying that I know what I did was wrong – misleading you and keeping the truth from you. I apologize for doing that. And for any other hurt I’ve caused. I can’t take back what happened, but I wanted to tell you to your face what your, uh, friendship has meant to me.”

Castiel takes another sip of tea and Dean can’t read his face, so he continues. “I think the main reason I never told you who I was at the café was because I was afraid. I know that neither of us ever said it in our messages, but when we made those plans, I was excited to meet you as a friend, but I was also hopeful that it may become something… more.”

Castiel’s eyebrows shoot up his forehead, but he doesn’t look upset. “Were you hoping it would be a date?”

“I’m not sure. I guess so,” Dean offers with a shrug. “But it was complicated enough with you being a guy and me not being out to anyone in my family. When you turned out to be, well, _you_, I just lost my nerve.”

“Is there anything about your life that isn’t influenced by your family and what they think?” Castiel asks, and it all but slaps Dean across the face. 

When Charlie asked him about what he lets his family control, he didn’t have a good answer. And now, months later, sitting with the man he feels more connected to than anyone else in the world, he still doesn’t know what to say. 

“Listen, Dean, I get it. This is the craziest situation I’ve ever heard of. If someone came to me and told me this story I would probably roll my eyes. And although you have been lying to me for the last two months, I honestly can’t say that I wouldn’t have done something very similar if I had known the truth and you hadn’t.” 

Dean immediately feels a rush of relief hearing Castiel admit that his actions weren’t as deplorable as he felt they were.

“I don’t expect you to forgive me right away, or maybe at all,” Dean says quickly, “but I hope that now that we both know, now that everything is out on the table, we might be able to try again.”

“What do you mean by ‘try again’?” Castiel asks, using his free hand to gesture air quotes next to his face. “Did you really hope that our meeting at the café would turn into a date?”

“Yeah,” Dean says hesitantly.

“Before you saw me? Just from our messages?”

“Yeah. Our letters have meant a lot to me. I mean, you were the first person I came out to. You’ve definitely made an impression on my life.” Castiel cracks a smile and Dean feels his stomach swoop with something other than nerves.

“Let me ask you something, Dean,” Castiel says. Dean is really getting addicted to hearing Castiel say his name. “If I weren’t sick, and I said it was okay, would you want to kiss me right now?”

“I – I, um,” Dean starts, unconsciously licking his lips.

“No, wait. Don’t answer that,” Castiel says, shaking his head and holding up one of his hands. “My head is starting to get fuzzy and I don’t think now is the time to make any rash decisions.”

“Right. Of course. You’re sick and need to get well,” Dean replies hurriedly, sitting further back in his chair and feeling heat rise to his cheeks.

“Yes, I’m going to head to bed and take a nap. I’ll see you out.” 

Castiel rises up from the couch and Dean finally gets a glimpse of his sleep pants. They are barely staying on, hanging dangerously low off of Castiel’s sharp hip bones. Dean wants to die a little, but he will save that for after he leaves. 

Castiel walks him to the door and opens it. “Thank you for the flowers,” he says quietly.

“You’re welcome. I hope you feel better soon.” Dean moves to leave, but before Castiel can close the door on him, he asks, “Would it be okay if I still write to you?”

Castiel stares at him, and Dean tries his hardest not to fidget or look away. 

“Yes, Dean. I was hoping you would.” Castiel gives him a small smile and closes the door, leaving Dean beaming in the hallway by himself.


	14. Time Heals, and So Does FanFic

Message from user – NY1967, Feb. 10th:

_I have a serious confession to make, and I hope you won’t hold it against me. I’ve been able to get away with it over the last few months due to the holidays, but now that they are over, I have to create strange and often false pretenses in order to feed my needs. The truth is… I love to bake. _

_ From Halloween through New Year’s Day, there are a million acceptable reasons to bake and share with people. But now that those times have passed us by, I’m having serious withdrawal. It may be from missing the eating part as well, but I honestly love the process. It is a science as well as an art, and it brings me so much joy to see that something I put time and love into makes someone else happy. _

_ My favorite has always been pie. It is just a perfect and versatile creation. You can make so many different types, the combinations are endless. Sweet, savory, maybe even a bit of both if you have ever tried apple pie with cheddar cheese on top (a delicacy in some places, but often misunderstood). If I had a valentine, I would bake them a pie. But, alas, that is not in the cards. Perhaps next year._

  
  


Message from user – bookshop-boy, Feb. 17th:

_I don’t know how much of the Supernatural series you have read (so spoiler alert if you haven’t gotten far), but in the fourth book, there is a character named Castiel. My father actually wrote this book before I was born, so I am named after the character rather than the character being named after me._

_ Castiel in the book is an angel, and angels are warriors for God. They are soldiers, creatures that are meant to fight for the righteous good and nothing else, really. My father wrote Castiel as an angel who begins to question. He knows all the rules and how to obey, he knows exactly what is expected of him, but he doesn’t know why. He doesn’t know the plan, and he is not meant to. But he begins to question why he is not meant to know the plan. He questions why he must follow the orders of someone he barely knows or understands. _

_ Castiel goes through a lot of changes during the series. I’ve often wondered if I could ever be like him. Someone who finds the courage to ask why, and the strength to find the answers no matter how ugly they may be. Sometimes I feel like I see some of Castiel in you. (And no, that is not innuendo.)_

  
  


Message from user – NY1967, Mar. 1st:

_Sometimes I worry about my little brother. You got to meet him when we came to your shop. Despite us being close, I don’t get to spend nearly as much time with him as I would like. I have my own place, and I get to see him maybe once or twice a week at best. I worry because I know how rough it can be to grow up with a father like ours. _

_ He is a very successful man, but you know well enough that this doesn’t mean that he is a good man. The more I reflect on what happened between us in a business sense, the more I see how much I am like my father despite my best efforts. My father values intelligence and cunning. He is a strategist, and a ruthless one at that. He tried to turn me into one, as well, and in a lot of ways, he has succeeded. _

_ But as I have started to stray from his teachings, I am more aware of his influence over my brother. Sammy has such a kind soul. I hope that he can keep it as he grows up. I hope that I can be a better influence for him._

  
  


Message from user – bookshop-boy, Mar. 2nd:

_I understand your concern. I don’t mean that to judge you or your family, but I feel your worries apply to a broader concern I have about the world in general. I’ve never been one for competition. I find it uncomfortable and distracting from real goals. I didn’t get to talk to your brother much when I met him, but he did give me the impression of being a young man of real substance. _

_ There is a quote I have seen floating around on this site: “When I was young, I admired clever people. Now that I am old, I admire kind people” (Rabbi Abraham Joshua Heschel). To me, being clever is only useful if you are kind. Cleverness without empathy, without emotional intelligence, with only selfishness, is how we end up with nonsense like _Atlas Shrugged_._

  
  


Message from user – NY1967, Mar. 15th:

_I finally got around to coming out to my brother today. I had been avoiding it for a while, assuming that it wasn’t necessary until I was actually dating a man, but then I realized that didn’t make sense. What if my brother needed to hear from me that being not straight was okay? I know that I probably needed to hear it when I was his age, and I didn’t. It’s probably part of the reason why I waited so long to admit it to myself. So, I bit the bullet and told him over dinner last night. I thought it was going to be awkward, but he was like, “Oh yeah, I knew that. Glad you figured it out.” _

_ So I was just sitting there, almost embarrassed for myself. A bit anticlimactic, but by the end of the night we were laughing about it. When I told him about you, he got really excited. That’s when I was definitely embarrassed. He certainly gave me some shit about what happened between us, but mostly he was amused by the whole thing. Said it could be a rom com. I wouldn’t know, since I never watch those, of course. _

_ I don’t mean to put any pressure on you, but Sammy thinks we would make a good match, and I gotta tell you, this kid is really smart. He is doing upper-level math already. So maybe we should trust his judgement. _

_ But all jokes aside, I want to thank you for helping me get here._

  
  


Message from user – bookshop-boy, Mar. 17th:

_I’m so glad coming out to your brother went well. Our own story may be unique, but it doesn’t hold a candle to the level of embarrassment that I had when I ended up coming out to my father. _

_ He was great about it, very accepting, but it had a very rocky start in that it sort of happened by accident. I won’t go into all the gory details, but he may have walked in on something he wasn’t supposed to see. And that may have left an image of me he didn’t want. There may have been another boy, some fuzzy handcuffs, and not a lot of clothes involved. I can’t be sure; it is all a little hazy at this point in my life. Needless to say, my father was a very consistent knocker after that incident._

  
  


Message from user – NY1967, Mar 18th:

_Wow. Just wow. I’m pretty sure I would have passed out with all of the blood in my body suddenly rushing to my face in shame. I’m so grateful to have never been walked in on during the act. I have certainly gotten myself into some interesting situations, though. Not to go into too much detail myself, but there may have been a night when undergarments were exchanged between certain parties involved. _

_ You have a blessed day, buddy, and stay out of trouble._

  
  


Message from user – bookshop-boy, Mar. 25th:

_As we have been on the theme of admitting things for the last week or so, I figured now is as good a time as any to tell you that I’ve been doing a lot of writing lately. Most of it is for a larger project I’m working on, but sometimes I need a break and I have fallen into the habit of writing erotica again. I had taken some time off while I was stressed, but now that things are all said and done, I’ve gotten back into to it full-force. _

_ I’ve never shared my erotica with anyone who actually knows me in person. I fear that would be just too much information, like seeing inside my head or my dreams. I thought about sharing it with Frank, but seeing as it takes the form of fanfiction, I was fairly certain he wouldn’t have had enough interest. _

_ However, since you have taken the initiative to be vulnerable, if you are so inclined you can look me up on AO3 with this same user name. And please, be gentle._

  
  


Message from user – NY1967, Mar. 29th:

_Be gentle, my ass! There is nothing gentle about that spanking Watson gave Sherlock in your latest fic! But, in all seriousness, holy fuck, that is hot. I have read and written many a fanfic in my time, but yours are right up there with the best. As the great philosopher Jayne Cobb said, “I’ll be in my bunk.”_

  
  


Castiel is finally enjoying the warming spring air on a bench in the relatively quiet park as he reads through the latest notes given to him by his editor, when a shadow is cast by a tall man in front of him. Castiel looks up and can’t stop his broad smile. 

“Hello, Dean.”

“Hiya, Cas. It’s been a long time,” Dean beams down at him, looking only slightly nervous about finally seeing him face to face again.

“Well, with all of the messages we have been sending, it doesn’t feel like it. What have you been up to? Please, sit down.” Castiel slides over to make room for Dean on the bench. 

“I’ve been trying to get a new project started, so that has been taking up most of my time,” he says as he takes a seat next to him. “I’m really glad I ran into you here. I’ve been thinking about asking to see you, but I didn’t want to disrupt the nice flow we have been having. I have to admit, I’m a little surprised how nicely things have been going between us, considering…” Dean moves his hands out in a vague circular gesture, seemingly trying to encapsulate all of the nonsense that has brought them to this point in time.

“I’ve been surprised myself,” Castiel muses. “I mean, we always had an easy time messaging each other before, but after what you told me, I was still mad about what happened. But the problem was,” Castiel chuckles lightly, “whenever you would write to me, I kept forgetting to be mad at you”

Dean gives off another beaming smile. “Well, I’m glad your memory has been failing you so spectacularly, then,” he says, earning another laugh from Castiel. “I don’t mean to push my luck, but would you be opposed to meeting me on purpose somewhere? Maybe tomorrow at the Italian place that’s down two streets from here at seven?”

“Well, well, well, Dean Winchester. You wouldn’t be trying to ask me on a date, would you?” Castiel teases, folding his arms across his chest and smirking.

“If that’s what we are calling it, then I’m in. What do you say?” Dean asks, hope brimming in his voice.

Castiel gazes back out at the park, watching as people make their way through their day. Castiel hasn’t dated anyone since Frank. He has been busy, sure, but he also hasn’t been looking at all. He’s had plenty of time to think about Dean these last few months, and every time Castiel thought he was about to just slowly let their correspondence die out, Dean would come back with another sweet message or funny story or insightful thought. 

Castiel can deny it all he wants, but deep down he knows that he has kept up their messages because he wants to see where this goes. He wants to see how Dean grows and evolves, and how Dean changes him. 

He wants to know Dean. He wants Dean.

“Okay, I can do that,” he finally answers as he turns back to look at his face. “At least this time, I’ll know it’s you when you walk in.”


	15. Hope For the Future

Dean is nervous. He’s really nervous. Put him in front of a room full of stockholders or a jumble of reporters at a press conference, and he doesn’t even break a sweat. But waiting outside the restaurant for Cas is giving him freakin’ heart palpitations. 

Charlie gave him a nice pep-talk while she helped him dress for the night. Dean is pretty sure it consisted of things like “be yourself, compliment him, but not too much, and don’t get too drunk,” but he can’t be sure of what else she said because he was too busy worrying. She put him in a nice flannel and some tight jeans. He wasn’t too sure about the look, but Charlie assured him it was sure to please his date.

Dean has never been one to be nervous before a date, and he isn’t sure if this nervousness is due to the fact that Cas is a man or because Dean actually really likes Cas. Dean has dated women he liked in the past, but no one ever gave him much of a spark. Some of the nerves are due to excitement, but those are hard to filter out right now.

Dean spots Cas making his way down the block, and after an initial wave of butterflies in his stomach, he takes a deep breath and greets him with an easy smile. He is pleased to see that Cas returns his smile. He is also pleased to see that Cas has decided to wear that trench coat Dean saw when he went over to his apartment months ago. It may be a bit outdated and too big, but it already brings a sense of hominess and connection to Dean from when he first saw it. When he takes it off as they make their way inside the restaurant, Dean admires the V-neck cut of his sweater, showing off his neck and clavicle. The deep gray-blue color compliments his eyes. It feels a little strange to be openly admiring another man’s appearance, but Dean reminds himself that he is allowed the indulgence.

After the waiter takes their drink orders and they both peruse the menu, Dean tries to open the conversation with something fun. “So, are you writing any new fics? I have been enjoying the ones I’ve read so far. You are quite prolific.”

Cas smiles a bit self-consciously, “Thank you, I’m glad you like them. I have one that I’ve been fiddling around with as a distraction, but most of the time I force myself to focus on my other project.”

“What project is that, exactly? Is it a secret?”

“Not quite a secret, but I haven’t told many people about it yet. I was contacted by my father’s old publisher. Since the series has gotten a spike of interest again, uh, thanks to you actually,” Dean’s face blushes slightly, but his heart is soaring, “he asked if I would be up for adding to the collection.”

“Wow, so you’re going to write more Supernatural novels?”

“Sort of. I’ll be starting a spin-off series. My father always talked about creating something from a different perspective besides ‘two white guys with daddy issues,’” Cas uses air-quotes and Dean’s heart melts a little.

The waiter comes by to take their order and then Dean says, “So who are the stories about in your spin-off?”

“Well, I’m not sure if you have read far enough in, but in some of the later ones, there is a cop who works in Bobby’s town named Jodie. She ends up with sort of a found family with some young women who are orphaned by supernatural circumstances. I’m telling stories about those women and their journey into the hunting life.”

“That sounds awesome! How far along are you? Would you be willing to give me a sneak peek?”

“I’m about three-quarters of the way through, and I don’t let people read my work until I’m on the second draft, at least. I was actually thinking that the woman who works for you, Charlie I think was her name, that she might have some good feedback for it, if she is willing.”

“Oh man, Charlie would love it! She and I are good friends, actually. Best friends really, if people our age are allowed to still say that,” Dean laughs a little self-consciously. “She is a huge sci-fi fan, and I know she would be excited about a woman-centered story. She is always good about keeping me aware of the disparities in representation in the books we carry.”

Castiel nods knowingly. “Yes, it is something that the company I keep often struggles with. I always loved books because they opened up new worlds, but it is difficult when there are no stories about someone like yourself. It isn’t hard to find books about straight white men, but finding LGBTQ characters or books by or about people of color, or books about women, despite the fact that they make up half of the population...” Castiel tries to contain his rambling, but this topic always ignites a spark in him. “Although I’m not a part of all of these groups, it is important to me to make sure they are heard and represented in stories.”

“You’re totally right. I have to admit, I wasn’t really aware of all of these issues most of my life, but once I met Charlie, she really wised me up.”

“She sounds like a great friend.”

Dean beams at Castiel, “She really is. She may get a bit over-excited at times, but I wouldn’t trade her for anything. She, um…. she actually helped me get ready for this date tonight,” Dean says, color spreading to his cheeks.

“Oh really?” Cas asks, grin spreading across his face. “The infamous Dean Winchester needs help dressing for a date with little old me? What? Are you nervous or something?” he teases.

“I mean… yeah, a bit,” Dean admits, with a sheepish smile and a hand rubbing the back of his neck. 

Cas’ smile falls a little in sympathy, “Why are you nervous? I’m sure you’ve been on plenty of dates, and I’m not exactly intimidating,” he adds incredulously.

“Well, in case you forgot, it took a lot to get here. It’s not like we just met at a party or something. And even if we had, there would be no way that I would have asked for your number and called you up for a date when I first met you. I mean, I was barely playing with the idea that I could be interested in men. I was nowhere near asking one out.”

“I see. You really have come a long way since we first met. We both have. I mean, if you asked me a year ago if I would be starting my own series, I would have scoffed at the thought.”

Their meals arrive and they start to eat. Dean’s nerves have subsided quite a bit. Talking with Cas is so easy, but it always makes him feel more vulnerable. Cas is so different than most of the people he meets in high society. There is always such a demand to posture and put up a façade of confidence and arrogance. Cas would never allow Dean to get away with that persona now; those charms have no place in a conversation with him. Dean is being challenged here, and not in the ways he usually is, and he finds he loves it.

“I know that what you went through at the end of last year was painful, and I know I’ve apologized before, but I really am sorry for my part in it.” Dean says and Cas waves his hand dismissively as he chews a mouthful of his carbonara. “But it is a bit strange how things have seemed to work out in their own way.”

“Yes, but I guess that is how life works, isn’t it? Things keep moving forward and you find a way to make it okay. I miss the store, a lot, but mostly because of the memories and the people. And the thing is, I still have those. I may not be able to go their physically, and we may not be a place for people in the city to enjoy, but forty-two years isn’t half bad. I’ve found it a bit… freeing, actually.”

“What do you mean?” Dean asks with a tilt of his head.

“In my old life, I was really living for someone else’s dreams, not my own. Now I’ve been pushed from the nest, and I can dare to live a different life.” Dean smiles at Cas who lets out a quiet sigh and twirls another bite of pasta onto his fork.

“I’ve been trying to do a bit of daring myself in that vein.”

“Oh, really? Are you going to be leaving your family’s company?”

“No, nothing as extreme as that, at least not right now. My grandfather has been as good as retired for years now, and I know my dad will be wanting to step away from some parts of the operation soon. I’m hoping that if he does, I can move someone else in, maybe expand leadership to include some non-Winchesters. Diversify a little and see what others can bring to the table.”

“That sounds like a good plan, but if you bring in other people, what would you be doing?”

“That’s the beauty of the idea. I could do something completely different,” Dean says, and Cas leans in with a hint of excitement on his face. “I’ve been thinking that the company should get more involved in charitable works. Maybe open up a foundation. Something that makes a difference besides selling cheap books.”

Cas leans back in his seat and crosses his arms in front of his chest. His smile is warm and he slowly shakes his head from side to side in disbelief. “Well, well, well. This night is just full of surprises. First I get to see your nerves and now your heart.” 

Dean’s blush spreads all the way to his ears, but his smile remains as Castiel continues. 

“I have to admit, when I didn’t know you were my Tumblr friend and I only knew you as ‘Dean Winchester – businessman and competition assassin,’ I didn’t really think you had much of a heart. But now that your real-life and online persona are merged, and with what you are saying now… I don’t know, Winchester, there may be hope for the human race yet.” 

Dean laughs with Cas before picking up his glass and offering a toast to “hope for the human race.”

Outside the restaurant after they have settled the bill, Dean finds himself in a small panic wondering what to expect for the end of the night. He’s been trying to make sure he doesn’t stare at Cas’ lips too much, but at this point it is almost all he can do despite himself. 

Cas is standing facing him, about to walk off in the opposite direction once they say their goodbyes. Dean is hoping for a kiss, but he is way too nervous to remember how to initiate that. With women the signs to him were clear, but this is so much more complicated than that.

Lucky for Dean, Cas can clearly read the distraught look on his face he is trying to hide. Cas takes a step forward into Dean’s personal space and says, “Just come here a sec,” before closing the distance between them.

The kiss is closed-mouthed and simple, but when Dean breathes in the scent of Cas as their lips touch, he is overwhelmed with a desire to draw him closer. 

He settles for grabbing the open sides of Cas’ trench coat to ground himself. Dean tilts his head more to slide and massage his lips against Cas’, earning a small sigh from him. After a few moments they pull away and Dean opens his eyes to see that Cas is slow to open his own.

“Thank you for the wonderful night,” Cas says quietly, not immediately moving out of Dean’s personal space.

“Yeah,” is all Dean says, but he is too high off their kiss to care about his ineloquence. 

“Here, uh, give me your phone,” Cas asks and Dean eagerly takes it out of his pocket. Cas puts his number in the phone and texts himself a winky-face emoji. “There, now you can ask me on another date.”

“Ah, I see. So that’s how this works?” Dean teases, but its bite is lessened by the huge grin on his face.

“Don’t worry, Dean. You’ll learn soon enough. And you have me to teach you.” 

Dean’s knees threaten to give at the implication of that last sentence, but he holds it together long enough to say goodnight before he truly embarrasses himself. 

They part ways and Dean doesn’t even make it twenty-four hours before he texts Cas asking him out for a second date.

  
  


Their second date takes them to Cas’ favorite sushi spot and then on a stroll around the neighborhood. Dean gets to walk Cas home, and they exchange a more heated kiss goodbye in front of his door. 

Dean feels Cas’ tongue press against his own and he doesn’t quite hold back a moan. When the sound escapes his throat he feels Cas’ hands on his hips. Not pulling him forward, but squeezing slightly. Dean lifts his hands to touch Cas’ jaw with his thumbs and cup his face and neck in his palms. 

Dean isn’t sure how long they make out in front of Cas’ door. It probably only lasts less than a minute, but it leaves him breathless. They pull away when Cas eases the grip he has on Dean’s hips. 

“Goodnight Dean. I look forward to seeing you again soon,” Cas says quietly before placing one last peck on Dean’s lips. He makes his way inside his apartment before Dean realizes he never even said anything back.

For their third date, Dean tries to turn things up a notch. He invites Cas over so he can cook for them. He makes sure the apartment is immaculate.

He is still staying at his father’s old bachelor pad. His father, true to his word (and, let’s face it – old habits die hard) has already moved into a new place with a new woman. The apartment is definitely nice, but not exactly Dean’s style, so he will have to let his personality shine through with his cooking instead. 

He is making gourmet burgers and a cherry pie for dessert. He puts fresh sheets on the bed and makes sure there are supplies in the side table drawer, but just the thought of using them makes his stomach fill with butterflies, so he isn’t sure they will see any use tonight.

Dean has been reading up on techniques for sex between two men. He knows he has read a ton of scenes which feature it before, but there is a big difference between fan fiction fucking and the real thing. 

The kisses between him and Cas have been running through his head all day. Dean knows he wants more; he just isn’t sure how he will feel when the possibilities are standing right in front of him.

When Cas arrives he is slightly out of breath. It had started to rain while he was walking to Dean’s place. His trench coat has damp shoulders and there is some water dripping from his hair. Cas removes his coat and runs his palm roughly over his head to shake out the moisture, leaving his hair more wild and sexy than usual. Dean takes a calming breath and ushers Cas into his kitchen.

“I have made you one of my signature dishes, so prepare yourself for a meal worthy of its own center spread in Bon Appetit magazine,” Dean announces as he starts bringing the dishes to the table that was already set.

Cas raises his eyebrows in interest and slides into one of the chairs. “Just _one_ of your signature dishes, you say? Does that mean you have a secret repertoire?”

“Oh, yes, my dear sir. I have many skills hidden up my sleeve,” Dean adds with a flourish of the dish towel as he places it back on the counter and joins Cas at the table.

“Up your sleeve? I’m sure that’s not the only place you are hiding skills,” Cas says and Dean could swear he saw him wink before turning his face to inspect the meal laid before him.

“Well, we will just have to find that out later, I guess. In the meantime, the burgers are ready now and the pie will be ready soon.” The blush on Dean’s face might give him away, but Cas doesn’t tease him further.

The burgers go over very well, almost too well. Cas is quite vocal with his enjoyment and Dean finds himself distracted by the moans he makes around mouthfuls. Once dinner is done and the pie is setting out to cool, Dean leads Cas into the living room to the sofa. 

Dean and Cas catch up about their work and families. Cas tells him that he finally finished his first draft and is ready to do his first read-through. Dean gets up to grab them a couple of beers from the fridge and when he returns he sits himself closer to Cas on the couch.

He throws his arm over the back and pulls his knee up onto the cushion so he can angle himself towards the other man. Cas takes a long sip from his bottle before mirroring Dean’s pose. Suddenly Dean realizes that his hand is only inches from Cas’. 

He stares at their proximity, but can’t quite get his hand to move and close the distance. Cas must notice, because he clears his throat quietly before reaching forward and placing his palm on top of Dean’s hand. The contact makes Dean’s stomach flip for a moment, and then he feels a pleasant warmth spread through him.

Being alone with a man he cares about, getting to touch him and be close to him; Dean never imagined he could find his way here. Cas caresses his fingers along the top of Dean’s hand and wrist, sending tingles down his arm. Dean is suddenly aware that they haven’t spoken for a minute or so, but it doesn’t feel awkward. It feels electric. He can feel the anticipation between them build like humidity in the air.

Dean tears his eyes away from their hands to look at Cas. His eyes are heavy lidded and his lips are slightly parted. Dean leans forward, and Cas meets him halfway to slide their lips together. This kiss is different than the first two. 

Before, they were chaste, starting slowly and building in trust and comfort. This kiss has instant heat. Before, Dean knew the kiss was an ending to their evenings; now, it seems like just the beginning of what is to come. 

Cas grips Dean’s wrist and brings his other hand around to slide behind his neck. Dean clasps onto Cas’ waist as he tilts his head and opens his mouth to welcome Cas’ tongue. Their tongues slide together and Dean pulls Cas’ hips closer to him. Dean wants as little space as possible between them.

Cas massages his tongue against Dean’s and moves his strong fingers through the short hairs at the back of his neck, sending tingles down Dean’s spine. There is a languid and sultry push and pull between them as the kiss intensifies. It takes Cas swinging his leg over the other side of Dean for him to realize that he has pulled the man on top of him without thinking about it. 

Dean breaks the kiss to catch his breath and he stares up at the gorgeous man straddling his lap. Cas looks back down at him through heavy lidded eyes, letting his hands cradle Dean’s face as he moves his thumb across his pink lips. Dean has his hands braced against Cas’ back and as he pulls him in against his heaving chest, Dean feels their hips align, and he can feel Cas’ arousal press against his own. Cas lets out a small huff of air at the contact and Dean wants to hear more, so much more.

“Tell me what you want, Dean,” Cas says quietly, but firmly as he continues to brush his thumb along Dean’s bottom lip. “Tell me what you’re ready for and I’ll let you have it.”

Dean melts into the back of the couch, letting out an almost undignified groan as he lets his hips buck up slightly into Cas. “I… I’m not sure.”

“It’s okay, Dean. I’ll take care of you.”

“I want… to touch you, to see you,” Dean manages to say, earning him a sexy smile from Cas as he leans back in to kiss him.

Cas moves his hands down to the front of Dean’s shirt and pulls back from the kiss to ask silent permission. Dean nods his head and Cas unbuttons his shirt and then slides his hands up across his stomach and chest before pushing it down off his shoulders. Dean leans forward, supporting Cas’ lower back with one hand as he removes one sleeve and then the other. 

Cas tosses the shirt to the side and then moves to pull his sweater over his head, Dean helps him lift it off and adds it to the pile of clothes slowly building. Dean runs his hands over Cas’ biceps, up to his shoulders, and drags this fingertips down the front of his sculpted chest. Dean lets his thumb graze over a nipple and Cas sucks in a quick breath.

Cas leans back in to lightly suck kisses into Dean’s neck as he continues to explore his chest with his hands. Dean isn’t sure if Cas is conscious of the slow grind he is doing in Dean’s lap, but Dean is very appreciative of it. He brings his hands down and around to Cas’ back and lets them sink lower until he can cup Cas’ perfect ass and pulls him tighter against himself.

The grinding continues and Dean starts to let out little moans and sighs. “Cas… I’m getting tired of wearing pants,” he groans out and Cas stops kissing his neck to lean his forehead on Dean’s shoulder and chuckle.

“Well, I do know of a solution to that problem. Would you like to remedy the situation?”

“Yes, please,” Dean quickly replies and moves his hands to the front of Cas’ pants. Cas leans back to give him room and brings his own hands down to undo Dean’s jeans. Dean’s breath starts to get a bit shaky once he can see the top of Cas’ black boxer briefs. He can see the outline of his hardness, but hesitates to make his next move.

Meanwhile, Cas has opened Dean’s jeans and run his palm over his stiff cock, letting the soft underwear slide over the hot, sensitive skin. Cas kisses Dean once more as he give his cock a few more strokes. 

“Let me make you feel good,” He whispers against his lips before pushing himself off his lap and sliding down to his knees between Dean’s legs. 

Cas hooks his fingers on the top of Dean’s pants and Dean lifts his hips, allowing Cas to pull the pants and underwear down and off his legs. Now Dean is naked on his couch with a topless Cas running his hands along the tops of his thighs and he is wondering how he got so lucky.

Cas bends forward to lick a slow, firm stripe from the base of his cock to the tip. When Cas’ tongue reaches just below the head of his cock it twitches and Dean lets out a quiet whimper. Cas smirks up at him before taking the head into his mouth and swirling his tongue around it. 

Dean moans and reaches out to run his fingers through Cas’ wild hair. Cas sinks down on his cock and brings a hand up to stroke the half that won’t fit in his mouth. He sets a rhythm sliding over him that leaves Dean panting as he fights to keep his eyes open to watch as pleasure slowly builds in his body.

Soon, Dean hears Cas rustling his clothes and then Dean leans forward to see that Cas has taken his own cock out and is stroking it with his free hand. Dean’s grip in Cas’ hair tightens and he feels his cock pulse with sensation. Dean is glad that Cas is getting something out of this, but Dean still wants more. He doesn’t want to feel so far away and so passive for their first time together. Dean pushes his nerves down and finds his voice.

“Wait. Come back up here, I want to touch you, too,” he says as he pulls Cas off his cock with a gratuitous pop. 

Cas looks up and nods with a warm smile. He stands and pushes his pants and underwear off before returning to his straddle across Dean’s lap. Both men moan as their cocks meet in a slippery glide against each other.

“God, Dean,” Cas squeezes his eyes shut, “you don’t know what you do to me.”

“But I want to do more,” Dean says as he puts his hand behind Cas’ head to bring him back down in a kiss. 

He snakes his other hand between them to grip their cocks together. Cas briefly breaks the kiss with a groan, but then comes back in with even more passion as he begins to thrust into Dean’s hand and against his cock.

The kiss gets more sloppy as both men dissolve into moans and sighs. Dean holds his grip around them as they both thrust into the friction, chasing their release. Dean slides his other hand down Cas’ back to grip and squeeze his ass. 

They pant against each other, foreheads pressed together, Dean’s thighs flexing more rapidly as he gets closer and closer. Dean feels his pleasure crest and he throws his head back against the couch. 

“Cas, fuck, Castiel, uhn, god!” he groans as his orgasm rips through his whole body. His cock pulses as thick ropes of cum splash over his stomach, the top of his hand, and Cas’ still thrusting cock.

“Yes, god yes, Dean! That’s it. I’m so close...,” Cas moans as he watches Dean’s face flex in pleasure. 

Cas doubles his efforts as Dean puts every last ounce of energy he has left into holding his grip around Cas. After a few more seconds Cas lets out a long groan as his release splatters over Dean’s stomach.

Cas slumps in Dean’s lap, letting his forehead rest against the back of the couch next to Dean’s shoulder. Once he catches his breath a couple minutes later he pushes himself up and makes his way to the bathroom to find a washcloth. 

He brings it back moist with warm water and cleans Dean’s torso and hand before dropping the cloth on the coffee table and sitting back down next to Dean. Dean weaves their fingers together and tries not to over think.

He takes stock of the night. He made a great meal. Check. They talked easily through the night. Check. They kissed. Check. They both had orgasms. Big check. They are holding hands and he doesn’t feel like he wants to run or kick him out. The biggest of checks.

“You doing okay?” Cas asks, his voice even lower than normal.

“Yeah, actually, I’m doing great. How are you?”

“I’m good. You did quite well… for a novice,” Cas teases with a smirk and Dean turns to face him.

“What? Are you surprised or something? Were your expectations really that low?” Dean quips.

Castiel runs his fingertips over Dean’s chest in gentle, random patterns. “Not so much low expectations, but I wasn’t sure how comfortable you would be. I didn’t want to get my hopes up.”

“Well, if these are the novice results, I certainly have a lot to hope for in the future,” Dean says as he leans forward to plant another kiss on Cas’ soft lips.


	16. Ready and Epilogue

“Are you sure about this? I’m happy to keep doing what we are doing if you are still nervous or apprehensive,” Castiel offers as he cuddles next to Dean in bed. 

They are both stripped down to their underwear at this point, but progress had stopped when Castiel needed to grab supplies from his bedside table. Castiel has lost track of which date this is, maybe their sixteenth? Possibly even more than that. The time they spend together has just grown more and more enjoyable with time. 

Castiel finds Dean easier to talk to than any other man he has dated. He also has great taste in entertainment, introducing Castiel to many new movies and bands. And despite Dean’s life-long involvement in “the book business,” Castiel still finds plenty of books to share with him.

“Dude, I told you I’m excited to do this. No need to treat me like I’m so fragile,” Dean says before leaning in to give Cas another kiss. “Also, sorry for calling you ‘dude’ in this situation.”

Castiel chuckles and kisses Dean again. Castiel knows that Dean is probably more nervous than he is letting on, but Castile has to admit that he is a little nervous himself. He wants to make this good for Dean, and he is feeling under a bit of pressure. 

Some of the tension is eased as Dean’s tongue presses against his and he pulls their hips together. Cas can feel Dean’s arousal pressing up against his own as they slowly grind against each other. Dean breaks the kiss to let out a moan, and Castiel presses their foreheads together, indulging in a little more grinding before he gets to the task at hand.

Castiel reluctantly pushes himself up so that he looms over Dean and reaches over to grab the lube off the side table and place it next to himself on the bed. He takes the waist of Dean’s boxers and pulls them down and off. Dean’s cock lays thick and heavy against his stomach as Castiel lowers himself down to kiss along Dean’s collar bone. 

He moves down his chest, lapping at his sensitive nipples. Castiel was very pleased when he discovered that little secret about Dean. He arches up into Castiel, gasping quietly as his chest flushes to a beautiful pink, bringing out his freckles. Castiel could spend all evening slowly working over Dean, but tonight they have a goal and he doesn’t want to disappoint.

Castiel moves further down Dean’s body, placing searing kisses along his torso until he reaches the apex of his hips. Castiel bends to kiss the base of Dean’s stiff cock and trails kisses along the length until he reaches the wet tip, swiping his tongue against the head and eliciting a groan from Dean lying against the pillows. 

Castiel pulls the tip of Dean’s cock into his mouth as he pops the cap on the lube bottle and squirts a generous amount onto his fingers and rubs them together to warm it. Castiel moves his mouth further down Dean’s cock as he moves his hand down between his legs and applies the lube over his hole. Dean twitches against him and gasps at the contact. 

Castiel keeps his mouth working over Dean’s cock as he slowly works him open. Dean lets out the most delicious sounds as Castiel moves his fingers inside him. Once Castiel has two fingers inside him comfortably, he searches out Dean’s prostate and is rewarded with a sharp gasp followed by a deep groan when he finds it. Castiel pops off Dean’s cock and looks up to watch his face as he brushes over his prostate again.

“Holy shit!” Dean moans as he throws his head back. Castiel smiles broadly. 

He keeps his fingers buried inside Dean as he pulls himself up to give him a deep kiss, swallowing down his moans. Castiel adds a third finger and Dean breaks their kiss with another gasp. “Oh fuck!”

“Still good?” Cas asks as he eases back a bit.

“Yeah, yeah, so good. Don’t stop.”

“I’ve got you, Dean.” Castiel stretches his fingers apart, making sure Dean is open and ready. “I think you’re good. Are you ready for me?”

“Yes. Want you,” Dean moans out, eyes shut tight.

Castiel takes a deep breath and removes his fingers from inside Dean, making the man shudder below him. He quickly removes his underwear and begins rolling a condom he grabs from the side table down his over-eager erection. 

Dean props himself up on his elbows to watch him with hunger in his eyes. Once the condom is securely on, Cas pours out another large dollop of lube and spreads it over himself. His hips cant up into his fist with the sensation. He has been denying himself any attention while he prepped Dean and now his cock is desperate for any friction.

“Should I stay like this, or do you want me in a different position?” Dean asks, not taking his eyes off Castiel’s hand on his cock.

“No, you can stay like that, let me just put a pillow under you,” Castiel says as he grabs one of the pillows Dean isn’t laying on. “It will make the angle better and then, then I can still see you,” Castiel adds with a warm smile.

Dean lifts up his ass and lets Cas slide the pillow underneath. Cas snakes his hands under his knees and over his thighs to pull him down the bed a few inches towards him. “There, is that okay?”

“Yeah, yeah this is good,” Dean smiles, almost shy.

Castiel leans back over him to give him a deep kiss. They both sigh and take a moment to let their mouths move against each other. Castiel moves his hips down between Dean’s thighs, and he feels the tip of his dick catch against Dean’s rim, making Dean let out a tiny whimper.

Castiel breaks the kiss to look down and line himself up. He gazes back up at Dean to lock their eyes as he slowly pushes in.

Dean tries, but he can’t keep his eyes open as the overwhelming fullness takes over him. Dean breaths through the stretch and when Castiel bottoms out, Castiel lets out a deep groan that makes Dean tingle all over his skin.

“Oh fuck, Cas,” Dean breaths as he waits for his body to adjust.

“Dean, you are so fucking tight,” Cas groans, and Dean feels a flash of lust hearing Cas swear. “Tell me when you’re ready for me to move.”

“Just, just give me a minute.”

“Of course, Dean. I want you to feel good. That’s all I want,” Castiel says, leaning down again to kiss along Dean’s jaw and down his neck.

Dean feels his body start to relax and he gives a tentative thrust upwards with his hips. Castiel moans and pulls his hips back to gently thrust back into him. They slowly build up a shallow rhythm as Dean’s body eases into the new sensations.

Castiel pushes himself farther up on his knees and pulls his cock almost completely out of Dean, before firmly thrusting back inside him. Dean throws his head back with a wild moan and Castiel smiles broadly. He begins thrusting in earnest, setting a pace that leaves Dean grasping at his forearms for leverage as he angles up to meet him.

Castiel lowers his torso to trap Dean’s leaking cock between them, giving him some added friction as Castiel works inside him. Castiel can feel his own pleasure building and adjusts his hips until he can be sure he is hitting Dean’s prostate.

“Oh fuck!” Dean shouts and Castiel can feel Dean’s cock twitch where it is trapped against his stomach.

“That’s it, Dean. I want you to feel so good,” Castiel pants.

“Yes, Cas, yes! Keep going, I’m getting close,” Dean whines as he gasps with each thrust against his prostate.

Castiel redoubles his efforts increasing his pace while maneuvering a hand between them to stroke Dean’s cock.

“Oh god! Just like that! Fuck, Cas!”

“Come on, Dean, let go for me,” Castiel groans as he feels his orgasm threatening to overtake him.

After a few more tight strokes Dean is tossing his head back and moaning as he paints their stomachs with his cum. 

With Dean tightening around him, it is all Castiel can do to hold himself up as his own orgasm rips through him and he empties into the condom inside Dean.

As the two men catch their breath, they begrudgingly separate to lie beside each other on the bed. Eventually Castiel has the strength to get up to find a warm wet washcloth to clean them up. After he drops it in the hamper, he pulls the blanket over them as Dean cuddles into his side and throws a leg over his thighs.

“Was it what you expected?” Castiel asks as he strokes Dean’s hand laying on his chest.

“I’m not actually sure what I expected, but it is definitely something I want to try again. Just not tonight”

Castiel chuckles and pulls Dean tighter against himself. “We’ve got plenty of time for more.”

  
  


_Three Years Later_

“Good evening distinguished guests, and thank you so much for joining us on this wonderful evening to support the Winchester Books Representation Matters Foundation,” Charlie announces to polite applause from the packed ballroom of finely dressed people. 

“As the foundation’s board chair, I have the privilege of introducing the man who is responsible for all of this. A man who I am proud to call both a boss and a friend. In these first two years alone, the foundation has already funded twenty-three new authors who have seen their work make it onto store shelves and libraries and schools all over the country. 

“These authors have crafted wonderful books that tell us the complex and important stories of characters from diverse backgrounds, races, sexual orientations, and gender identities. These stories are so important for us to hear, especially for those who have never seen themselves as the main character. For those who have only ever been the side-kick, or in the background, or disposable, or simply not there at all. 

“The foundation makes it easier to give these stories the spotlight that they deserve. And so please help me in welcoming the organization’s director and founder, Dean Winchester.”

Dean leans over to give Cas a peck on the cheek as he stands to make his way to the podium as the audience cheers. He accepts an enthusiastic hug from Charlie before she takes her seat and he pulls out his speech from the inside pocket of his tux.

“Thank you all for joining us and giving so generously to our cause. I’m not one for long speeches and I know everyone would rather enjoy the food and band, so I’ll keep this short and sweet. 

“I’ve been asked many times what inspired me to start all this. And while there is no denying that the brilliant woman who just introduced me had a lot to do with it, there is someone else that I feel deserves quite a lot of credit for helping me realize how I can use my privilege and standing to make a difference. 

“When I first met Castiel Shurley, I was a guy who was good at my job, but not a guy who really had much other purpose in life besides that. I was smart enough and bold enough to stay at the top of my game, but in all sense of the word, I was drifting. I was moving through life letting other things push me to where I was going. I was letting other people tell me what was important and what was true without taking much time to question it. When I met Castiel, suddenly I was challenged in a whole new way. I was forced to defend my choices and my life to someone who is not only smart and dedicated and righteous, but also kind, hopeful, and patient. Someone who showed me that compartmentalizing your life only ends up compartmentalizing your self.

“One cannot live as their authentic self if they are forced to hide parts of themselves away. One cannot live their truth if they’ve only ever seen or read or heard a truth that is nothing like their own. One cannot build a solid foundation of confidence and pride if the only reflections of themselves that they see are broken, or incomplete, or misunderstood.

“Castiel helped me see that my whole self is good enough. And we all need an angel like Castiel in our lives; one to help us see ourselves for who we truly are and what we can become. And so, to make sure that more young adults get the chance to see themselves as the main character in their own lives, I am using my privilege to make sure their stories are available for all to enjoy. So thank you to my two best inspirations, my dear friend Charlie Bradbury, and my dear husband Castiel Shurley. You both make me a better man. Thank you all again for coming out tonight. Have a great time and get home safe.”

Dean smiles and waves to the crowd as he makes a quick exit off the stage. Castiel is waiting for him back at their table with tears in his eyes. Dean knows that the guy is a sap, but he can’t help but love him.


End file.
